Sulfonamide derivatives, insecticides for agricultural and horticultural use, and usage thereof

ABSTRACT

Sulfonamide derivatives represented by general formula (I) or salts thereof; insecticides for agricultural and horticultural use containing the same as the active ingredient; and usage thereof:  
                 
 
[wherein A is optionally substituted (C 1 -C 6 )alkylene, (C 3 -C 6 )alkenylene or the like; R 1  is H, optionally substituted (C 1 -C 6 )alkyl, (C 3 -C 6 )alkenyl, (C 3 -C 6 )cycloalkyl or the like; R 2 , R 3  and R 4  are each H, (C 1 -C 6 )alkyl, (C 3 -C 6 )alkenyl or the like, or R 2  and A or R 2  and R 1  may form a 3- to 8-membered ring which may be interrupted by one to three atoms selected from among Of S and N; Q is C or N; X and Y are each halogen, CN, NO 2 , (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl or the like; m is 0 to 2; n is 0 to 3; and two adjacent Xs or Ys on the aromatic ring may be united to form a fused ring]. The compounds exhibit excellent insecticidal activity against insect pests resistant to existing pesticides even when applied in dosages lower than those of similar pesticides.

TECHNICAL FIELD

The present invention relates to sulfonamide derivatives or salts thereof, agricultural and horticultural insecticides containing any of said compounds as an active ingredient, and their usage.

BACKGROUND ART

Compounds analogous to the sulfonamide derivatives of the present invention have been known to be useful as agricultural and horticultural insecticides (see, for example, JP-A-11-240857 or JP-A-2001-131141). These references, however, do not describe working examples, physical properties and the like with respect to the compounds represented by general formula (I) of the present invention.

The production of agricultural and horticultural crops and the like is still badly damaged by insect pests and the like, and the development of a novel agricultural and horticultural insecticide is desired because of, for example, the appearance of insect pests resistant to existing chemicals. In addition, because of the increased population of aged farmers, and the like, various labor-saving application methods are desired and the development of an agricultural and horticultural insecticide having properties suitable for the application methods is desired.

DISCLOSURE OF THE INVENTION

The present inventors earnestly investigated in order to develop a novel agricultural and horticultural insecticide, and consequently found that the sulfonamide derivatives represented by general formula (I) or salts thereof of the present invention are novel compounds not known in any literature and are excellent agricultural and horticultural insecticides which are effective at a lower dosage as compared with the analogous compounds disclosed in the above prior art references, whereby the present invention has been accomplished.

That is, the present invention relates to sulfonamide derivatives represented by general formula (I), or salts thereof:

wherein A is a (C₁-C₆)alkylene group; a substituted (C₁-C₆)alkylene group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups and di(C₁-C₆)alkylamino groups whose (C₁-C₆)alkyl groups may be the same or different; a (C₃-C₆)alkenylene group; a substituted (C₃-C₆)alkenylene group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups and di(C₁-C₆)alkylamino groups whose (C₁-C₆)alkyl groups may be the same or different; a (C₃-C₆)alkynylene group; or a substituted (C₃-C₆)alkynylene group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups and di(C₁-C₆)alkylamino groups whose (C₁-C₆)alkyl groups may be the same or different; any saturated carbon atom in the (C₁-C₆)alkylene group, substituted (C₁-C₆)alkylene group, (C₃-C₆)alkenylene group, substituted (C₃-C₆)alkenylene group, (C₃-C₆)alkynylene group or substituted (C₃-C₆)alkynylene group may be substituted by a (C₂-C₅)alkylene group so as to form a (C₃-C₆)cycloalkane ring, and any two carbon atoms in the (C₂-C₆)alkylene group, substituted (C₂-C₆)alkylene group, (C₃-C₆)alkenylene group or substituted (C₃-C₆)alkenylene group may be taken together with an alkylene group or an alkenylene group so as to represent a (C₃-C₆)cycloalkane ring or a (C₃-C₆)cycloalkene ring;

R¹ is a hydrogen atom; a (C₁-C₆)alkyl group; a substituted (C₁-C₆)alkyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, hydroxyl group, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, mono(halo(C₁-C₆)alkyl)amino groups, di(C₁-C₆)alkylamino groups whose (C₁-C₆)alkyl groups may be the same or different, di(halo(C₁-C₆)alkyl)amino groups whose halo(C₁-C₆)alkyl groups may be the same or different, (C₁-C₆)alkoxycarbonyl groups, (C₁-C₆)alkylaminocarbonyl groups, (C₁-C₆)alkylcarbonyloxy groups, phenoxy group, substituted phenoxy groups having one or more substituents which may be the same or different and are selected from halogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups and (C₁-C₆)alkoxycarbonyl groups, phenylthio group, substituted phenylthio groups having one or more substituents which may be the same or different and are selected from halogen atoms, (C₁-C₆)alkyl groups, halo (C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo (C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups and (C₁-C₆)alkoxycarbonyl groups, phenyl group, substituted phenyl groups having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups whose (C₁-C₆)alkyl groups may be the same or different, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups and (C₁-C₆)alkoxycarbonyl groups, pyridyl group, and substituted pyridyl groups having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups whose (C₁-C₆)alkyl groups may be the same or different, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups and (C₁-C₆)alkoxycarbonyl groups; a (C₃-C₆)alkenyl group; a halo(C₃-C₆)alkenyl group; a (C₃-C₆)alkynyl group; a halo(C₃-C₆)alkynyl group; a (C₃-C₆)cycloalkyl group; a hydroxyl group; a (C₁-C₆)alkoxy group; a halo(C₁-C₆)alkoxy group; an amino group; a mono(C₁-C₆)alkylamino group; a mono(halo(C₁-C₆)alkyl)amino group; a di(C₁-C₆)alkylamino group whose (C₁-C₆)alkyl groups may be the same or different; a di(halo(C₁-C₆)alkyl)amino group whose halo(C₁-C₆)alkyl groups may be the same or different; a (C₁-C₆)alkylcarbonylamino group; a phenylamino group; a substituted phenylamino group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, mono(halo(C₁-C₆)alkyl)amino groups, di(C₁-C₆)alkylamino groups whose (C₁-C₆)alkyl groups may be the same or different, di(halo(C₁-C₆)alkyl)amino groups whose halo(C₁-C₆)alkyl groups may be the same or different, (C₁-C₆)alkoxycarbonyl groups and (C₁-C₆)alkylaminocarbonyl groups; a benzoylamino group; a substituted benzoylamino group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, mono(halo(C₁-C₆)alkyl)amino groups, di(C₁-C₆)alkylamino groups whose (C₁-C₆)alkyl groups may be the same or different, di(halo(C₁-C₆)alkyl)amino groups whose halo(C₁-C₆)alkyl groups may be the same or different, (C₁-C₆)alkoxycarbonyl groups and (C₁-C₆)alkylaminocarbonyl groups; —N═C(T¹)T² (wherein each of T¹ and T², which may be the same or different, is a hydrogen atom, a (C₁-C₆)alkyl group, a halo(C₁-C₆)alkyl group, a phenyl group or a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, mono(halo(C₁-C₆)alkyl)amino groups, di(C₁-C₆)alkylamino groups whose (C₁-C₆)alkyl groups may be the same or different, di(halo(C₁-C₆)alkyl)amino groups whose halo(C₁-C₆)alkyl groups may be the same or different, (C₁-C₆)alkoxycarbonyl groups and (C₁-C₆)alkylaminocarbonyl groups); a phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, mono(halo(C₁-C₆)alkyl)amino groups, di(C₁-C₆)alkylamino groups whose (C₁-C₆)alkyl groups may be the same or different, di(halo(C₁-C₆)alkyl)amino groups whose halo(C₁-C₆)alkyl groups may be the same or different, (C₁-C₆)alkoxycarbonyl groups and (C₁-C₆)alkylaminocarbonyl groups; a pyridyl group; or a substituted pyridyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, mono(halo(C₁-C₆)alkyl)amino groups, di(C₁-C₆)alkylamino groups whose (C₁-C₆)alkyl groups may be the same or different, di(halo(C₁-C₆)alkyl)amino groups whose halo(C₁-C₆)alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups;

each of R², R³ and R⁴, which may be the same or different, is a hydrogen atom, a (C₁-C₆)alkyl group, a (C₃-C₆)alkenyl group, a (C₃-C₆)alkynyl group, a (C₁-C₄)alkoxy(C₁-C₄)alkyl group or a (C₁-C₄)alkylthio(C₁-C₄)alkyl group, R² being able to bind to A or R¹ to form a 3- to 8-membered ring which may contain one to three atoms that may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, and which ring may have one or more substituents that may be the same or different and are selected from halogen atoms, (C₁-C₆)alkyl groups and (C₁-C₆)alkoxy groups, and R² being able to be taken together with R¹ to represent ═C(T³)T⁴ (wherein each of T³ and T⁴, which may be the same or different, is a hydrogen atom, a (C₁-C₆)alkyl group, a halo(C₁-C₆)alkyl group, a (C₁-C₆)alkoxy group, a halo(C₁-C₆)alkoxy group, an amino group, a mono(C₁-C₆)alkylamino group, a di(C₁-C₆)alkylamino group whose (C₁-C₆)alkyl groups may be the same or different, a mono(halo(C₁-C₆)alkyl)amino group, a di(halo(C₁-C₆)alkyl)amino group whose halo(C₁-C₆)alkyl groups may be the same or different, a phenyl group or a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, mono(halo(C₁-C₆)alkyl)amino groups, di(C₁-C₆)alkylamino groups whose (C₁-C₆)alkyl groups may be the same or different, di(halo(C₁-C₆)alkyl)amino groups whose halo(C₁-C₆)alkyl groups may be the same or different, (C₁-C₆)alkoxycarbonyl groups and (C₁-C₆)alkylaminocarbonyl groups);

Q is a carbon atom or a nitrogen atom;

each of Xs, which may be the same or different, is a halogen atom, a cyano group, a nitro group, an amino group, a (C₁-C₆)alkyl group, a halo(C₁-C₆)alkyl group, a (C₂-C₆)alkenyl group, a halo(C₂-C₆)alkenyl group, a (C₂-C₆)alkynyl group, a halo(C₃-C₆)alkynyl group, a (C₁-C₆)alkoxy group, a halo(C₁-C₆)alkoxy group, a (C₁-C₆)alkylcarbonyloxy group, a halo(C₁-C₆)alkylcarbonyloxy group, a (C₁-C₆)alkylthio group, a halo(C₁-C₆)alkylthio group, a (C₁-C₆)alkylsulfinyl group, a halo(C₁-C₆)alkylsulfinyl group, a (C₁-C₆)alkylsulfonyl group, a halo(C₁-C₆)alkylsulfonyl group, a (C₁-C₆)alkylsulfonyloxy group, a halo(C₁-C₆)alkylsulfonyloxy group, a mono(C₁-C₆)-alkylamino group, a mono(halo(C₁-C₆)alkyl)amino group, a di(C₁-C₆)alkylamino group whose (C₁-C₆)alkyl groups may be the same or different, a di(halo(C₁-C₆)alkyl)amino group whose halo(C₁-C₆)alkyl groups may be the same or different, a (C₁-C₆)alkylcarbonylamino group, a halo(C₁-C₆)alkylcarbonylamino group, a (C₁-C₆)alkylsulfonylamino group or a halo(C₁-C₆)alkylsulfonylamino group,

further, two adjacent Xs on the aromatic ring being able to be taken together to represent a fused ring that may have one or more substituents which may be the same or different and are selected from halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, mono(halo(C₁-C₆)alkyl)amino groups, di(C₁-C₆)alkylamino groups whose (C₁-C₆)alkyl groups may be the same or different, and di(halo(C₁-C₆)alkyl)amino groups whose halo(C₁-C₆)alkyl groups may be the same or different, m is an integer of 0 to 2;

each of Ys, which may be the same or different, is a halogen atom; a cyano group; a nitro group; a hydroxyl group; a formyl group; a (C₁-C₆)alkyl group; a hydroxy(C₁-C₆)alkyl group; a (C₁-C₆)alkoxy(C₁-C₆)alkyl group; a halo(C₁-C₆)alkoxy(C₁-C₆)alkyl group; a halo(C₁-C₆)alkyl group; a hydroxyhalo(C₁-C₆)alkyl group; a (C₁-C₆)alkoxyhalo(C₁-C₆)alkyl group; a halo(C₁-C₆)alkoxyhalo(C₁-C₆)alkyl group; a (C₁-C₆)alkoxy group; a halo(C₁-C₆)alkoxy group; a halo(C₁-C₆)alkoxyhalo(C₁-C₆)alkoxy group; a (C₁-C₆)alkylthio group; a halo(C₁-C₆)alkylthio group; a (C₁-C₆)alkylsulfinyl group; a halo(C₁-C₆)alkylsulfinyl group; a (C₁-C₆)alkylsulfonyl group; a halo(C₁-C₆)alkylsulfonyl group; a halo(C₁-C₆)alkoxyhalo(C₁-C₆)alkylthio group; a halo(C₁-C₆)alkoxyhalo(C₁-C₆)alkylsulfinyl group; a halo(C₁-C₆)alkoxyhalo(C₁-C₆)alkylsulfonyl group; a phenoxy group; a substituted phenoxy group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups; a phenylthio group; a substituted phenylthio group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups; a pyridyloxy group; or a substituted pyridyloxy group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups,

further, two adjacent Ys on the aromatic ring being able to be taken together to represent a fused ring that may have one or more substituents which may be the same or different and are selected from halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo (C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo (C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, mono(halo(C₁-C₆)alkyl)amino groups, di(C₁-C₆)alkylamino groups whose (C₁-C₆)alkyl groups may be the same or different, and di(halo(C₁-C₆)alkyl)amino groups whose halo(C₁-C₆)alkyl groups may be the same or different, and n is an integer of 0 to 3; an agricultural and horticultural insecticide containing said compound as an active ingredient, and a method of using the same.

MODE FOR CARRYING OUT THE INVENTION

In the definition of general formula (I) for the sulfonamide derivative of the present invention, the term “halogen atom” means a chlorine atom, a bromine atom, an iodine atom or a fluorine atom. The term “(C₁-C₆)alkyl” means a linear or branched alkyl group of 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl, n-hexyl or the like. The term “halo(C₁-C₆)alkyl” means a substituted linear or branched alkyl group of 1 to 6 carbon atoms having as the substituent(s) one or more halogen atoms which may be the same or different. The term “(C₃-C₆)cycloalkyl” means a cyclic alkyl group of 3 to 6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or the like. The term “(C₁-C₆)alkylene” means a linear or branched alkylene group of 1 to 6 carbon atoms, such as methylene, ethylene, propylene, trimethylene, dimethylmethylene, tetramethylene, isobutylene, dimethylethylene or the like. The term “(C₂-C₆)alkenylene” means a linear or branched alkenylene group of 2 to 6 carbon atoms. The term “(C₂-C₆)alkynylene” means a linear or branched alkynylene group of 2 to 6 carbon atoms.

The “fused ring” includes, for example, naphthalene ring, tetrahydronaphthalene ring, indene ring, indane ring, quinoline ring, quinazoline ring, chroman ring, isochroman ring, indole ring, indoline ring, benzodioxane ring, benzodioxole ring, benzofuran ring, dihydrobenzofuran ring, benzothiophene ring, dihydrobenzothiophene ring, benzoxazole ring, benzothiazole ring, benzimidazole ring and indazole ring.

The salts of the sulfonamide derivative represented by general formula (I) of the present invention include, for example, inorganic acid salts such as hydrochloride, sulfate, nitrate, phosphate and the like; organic acid salts such as acetate, fumarate, maleate, oxalate, methanesulfonate, benzenesulfonate, p-toluenesulfonate and the like; and salts with a sodium ion, potassium ion, calcium ion or the like.

The sulfonamide derivative of general formula (I) of the present invention contains one or more asymmetric carbon atoms or asymmetric centers in its structural formula in some cases and has two or more optical isomers and diastereomers in some cases. The present invention also includes all of the individual optical isomers and mixtures consisting of these isomers in any ratio. The sulfonamide derivative of general formula (I) of the present invention has two or more geometrical isomers due to one or more carbon-carbon double bonds or carbon-nitrogen double bonds in its structural formula in some cases. The present invention also includes all of the individual geometrical isomers and mixtures consisting of these isomers in any ratio.

In the sulfonamide derivative of general formula (I) of the present invention, A is particularly preferably a (C₁-C₆)alkylene group; R¹ is preferably a hydrogen atom, a (C₁-C₆)alkyl group, a substituted (C₁-C₆)alkyl group, a (C₃-C₆)alkenyl group, a (C₃-C₆)alkynyl group, a phenyl group or a substituted phenyl group, and is particularly preferably a (C₁-C₆)alkyl group, a (C₁-C₆)alkylthio(C₁-C₆)alkyl group, a (C₁-C₆)alkylsulfinyl(C₁-C₆)alkyl group or a (C₁-C₆)alkylsulfonyl(C₁-C₆)alkyl group; each of R², R₃ and R⁴ is preferably a hydrogen atom or a (C₁-C₆)alkyl group; Q is preferably a carbon atom or a nitrogen atom, particularly preferably a carbon atom; X is preferably a halogen atom, a nitro group, a (C₁-C₆)alkyl group, a halo(C₁-C₆)alkyl group, a halo(C₁-C₆)alkoxy group, a (C₁-C₆)alkylcarbonyloxy group, a (C₁-C₆)alkylsulfonyloxy group or a halo(C₁-C₆)alkylsulfonyloxy group, and is particularly preferably a halogen atom; m is preferably 1 or 2, particularly preferably 1; Y is preferably a halogen atom, a (C₁-C₆)alkyl group, a halo(C₁-C₆)alkoxy(C₁-C₆)alkyl group, a halo(C₁-C₆)alkyl group, a hydroxyhalo(C₁-C₆)alkyl group, a (C₁-C₆)alkoxyhalo(C₁-C₆)alkyl group, a halo(C₁-C₆)alkoxyhalo(C₁-C₆)alkyl group, a (C₁-C₆)alkoxy group or a halo (C₁-C₆)alkoxy group, and is particularly preferably a (C₁-C₆)alkyl group or a halo(C₁-C₆)alkyl group; and n is preferably an integer of 1 to 3, particularly preferably 2.

The sulfonamide derivative of general formula (I) of the present invention can be produced, for example, by any of the production processes schematically shown below, but these processes are not intended in any way to limit the scope of the present invention. Production Processes

wherein A, R¹ to R⁴, X, Y, n, m and Q are as defined above.

The production can be carried out by the above reactions according to the process disclosed in J. Med. Chem., 10, 982 (1967), JP-A-11-240857, JP-A-2001-131141 or the like. That is, a phthalic anhydride of general formula (II) is allowed to react with an amine of general formula (III) in the presence of an inert solvent and in the presence or absence of a base or an acid catalyst to obtain a phthalamide of general formula (V-1). When R⁴ is a hydrogen atom in the phthalamide (V-1), the phthalamide (V-1) is converted to an isoimide derivative of general formula (VI-1) by condensation in the presence of a condensing agent and an inert solvent and in the presence or absence of a base after or without isolating the phthalamide (V-1), and the isoimide derivative (VI-1) is allowed to react with a sulfamoylamine of general formula (IV) in the presence of an inert solvent and in the presence or absence of a base or an acid catalyst after or without isolating the isoimide derivative (VI-1), whereby the sulfonamide derivative of general formula (I) can be produced. When R⁴ is a substituent other than a hydrogen atom in the phthalamide (V-1), the sulfonamide derivative of general formula (I) can be produced by condensing the phthalamide (V-1) with a sulfamoylamine of general formula (IV) in the presence of a condensing agent and an inert solvent and in the presence or absence of a base after or without isolating the phthalamide (V-1).

In addition, a phthalic anhydride of general formula (II) is allowed to react with a sulfamoylamine of general formula (IV) in the presence of an inert solvent and in the presence or absence of a base or an acid catalyst to obtain a phthalamide of general formula (V-2). When R³ is a hydrogen atom in the phthalamide (V-2), the phthalamide (V-2) is converted to an isoimide derivative of general formula (VI-2) by condensation in the presence of a condensing agent and an inert solvent and in the presence or absence of a base after or without isolating the phthalamide (V-2), and the isoimide derivative (VI-2) is allowed to react with an amine of general formula (III) in the presence of an inert solvent and in the presence or absence of a base or an acid catalyst after or without isolating the isoimide derivative (VI-2), whereby the sulfonamide derivative of general formula (I) can be produced. When R³ is a substituent other than a hydrogen atom in the phthalamide (V-2), the sulfonamide derivative of general formula (I) can be produced by condensing the phthalamide (V-2) with an amine of general formula (III) in the presence of a condensing agent and an inert solvent and in the presence or absence of a base after or without isolating the phthalamide (V-2).

1. General Formula (II)→General Formula (V-1) or General Formula (V-2)

The acid usable in this reaction includes, for example, organic acids such as acetic acid, trifluoroacetic acid, etc.; and inorganic acids such as hydrochloric acid, sulfuric acid, etc. As to the amount of the acid used, the acid may be used in an amount properly chosen in the range of a catalytic amount to excess moles per mole of the phthalic anhydride of general formula (II). The base includes, for example, organic bases such as triethylamine, pyridine, etc.; and inorganic bases such as potassium carbonate, sodium hydrogencarbonate, sodium carbonate, sodium hydroxide, etc. As to the amount of the base used, the base may be used in an amount properly chosen in the range of a catalytic amount to excess moles per mole of the phthalic anhydride of general formula (II).

As the inert solvent used in the reaction, any inert solvent may be used so long as it does not markedly inhibit the progress of the reaction. There can be exemplified inert solvents including, for example, aromatic hydrocarbons such as benzene, toluene, xylene, etc.; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, etc.; halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, etc.; acyclic or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, etc.; esters such as ethyl acetate, etc.; amides such as dimethylformamide, dimethylacetamide, etc,; acids such as acetic acid, etc.; dimethyl sulfoxide; and 1,3-dimethyl-2-imidazolidinone. These inert solvents may be used singly or as a mixture of two or more thereof.

Since the reaction is an equimolar reaction, it is sufficient that the reactants are used in equimolar amounts, though either of them may be used in excess.

As to the reaction temperature, the reaction can be carried out at room temperature to the boiling point of the inert solvent used. Although the reaction time is varied depending on the scale of reaction and the reaction temperature, the reaction may be carried out for a period ranging from several minutes to 48 hours.

After completion of the reaction, the desired compound may be used in the subsequent reaction either after isolation from the reaction system containing the desired compound by a conventional method, or without isolation.

The phthalic anhydride of general formula (II) can be produced by the process described in J. Org. Chem., 52, 129 (1987), J. Am. Chem. Soc., 51, 1865 (1929), J. Am. Chem. Soc., 63, 1542 (1941) or the like.

2. General Formula (V-1) or General Formula (V-2)→General Formula (I)

As the inert solvent used in this reaction, any inert solvent may be used so long as it does not markedly inhibit the progress of the reaction. There can be exemplified inert solvents including, for example, halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, etc.; acyclic or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, etc.; and nitrites such as acetonitrile, etc. These inert solvents may be used singly or as a mixture of two or more thereof.

As the condensing agent used in the reaction, any condensing agent may be used so long as it is used in conventional amide production. The condensing agent includes, for example, trifluoroacetic anhydride, chlorocarbonates, Mukaiyama reagent (2-chloro-N-methylpyridinium iodide), DCC (1,3-dicyclohexylcarbodiimide), CDI (carbonyl diimidazole) and DEPC (diethyl cyanophosphonate). As to the amount of the condensing agent used, the condensing agent may be used in an amount properly chosen in the range of 1 mole to excess moles per mole of the phthalamide of general formula (V-1) or (V-2).

The base usable in the reaction includes, for example, organic bases such as triethylamine, pyridine, etc.; and inorganic bases such as potassium carbonate, etc. As to the amount of the base used, the base may be used in an amount properly chosen in the range of 1 mole to excess moles per mole of the phthalamide of general formula (V-1) or (V-2).

As to the reaction temperature, the reaction can be carried out at 0° C. to the boiling point of the inert solvent used. Although the reaction time is varied depending on the scale of reaction and the reaction temperature, the reaction may be carried out for a period ranging from several minutes to 48 hours.

After completion of the reaction, the desired compound is isolated from the reaction system containing the desired compound by a conventional method, and if necessary, purified by recrystallization, column chromatography, etc., whereby the desired compound can be produced.

3. General Formula (V-1)→General Formula (VI-1), or General Formula (V-2)→General Formula (VI-2)

In the case of this reaction, the desired compound can be produced according to, for example, the process described in J. Med. Chem., 10, 982 (1967).

After completion of the reaction, the desired compound may be used in the subsequent reaction either after isolation from the reaction system containing the desired compound by a conventional method, or without isolation.

4. General Formula (VI-1) or General Formula (VI-2)→General Formula (I)

In the case of this reaction, the desired compound can be produced in the same manner as in the item 1.

After completion of the reaction, the desired compound is isolated from the reaction system containing the desired compound by a conventional method, and if necessary, purified by recrystallization, column chromatography, etc., whereby the desired compound can be produced.

The sulfamoylamine (IV) as starting material can be produced according to, for example, any of the processes known in literature and schematically shown below.

wherein R¹, R², R³ and A are as defined above, R⁵ is a protecting group such as a benzyloxycarbonyl group, t-butoxycarbonyl group or alkylsilyl group, R⁶ is a (C₁-C₆)alkyl group, each of L¹, L² and L³ is a leaving group such as a halogen atom, Met is a metal atom such as sodium or potassium, and Z is a hydrogen atom, a (C₁-C₆)alkyl group or a benzyl group. (A) General Formula (VII-1)→General Formula (IV)

An amine derivative of general formula (VII-1) is allowed to react with a thiol to obtain a thioalkylamine derivative (VIII-1), according to the method described in J. Am. Chem. Soc., 58, 1348 (1936), J. Am. Chem. Soc., 60, 1486 (1938) or the like. The thioalkylamine derivative is allowed to react with a halogen after or without isolation of the derivative to obtain a sulfonyl halide derivative of general formula (IX). The sulfonyl halide derivative is allowed to react with an amine of general formula (X) to obtain a sulfonamide derivative of general formula (IV-1), according to the method described in Synthesis, 1970, 545, J. Organic Chem., 21, 667 (1956) or the like. The sulfonamide derivative is subjected to deprotection reaction according to a conventional method, whereby the sulfamoylamine of general formula (IV) can be produced.

(B) General Formula (VII-2)→General Formula (IV)

A disulfide derivative of general formula (VII-2) is converted to a sulfenic acid ester derivative (VIII-2) according to the method described in Synth. Commun., 27, 1321 (1997), Synthesis, 1988, 252 or the like. The sulfenic acid ester derivative is hydrolyzed after or without isolation and the hydrolyzate is allowed to react with a halogen according to the method described in J. Am. Chem. Soc., 45, 1068 (1923) or the like to obtain a sulfonyl halide derivative of general formula (IX). Thereafter, the sulfamoylamine of general formula (IV) can be produced in the same manner as in (A).

(C) General Formula (VII-3)→General Formula (IV)

An amine derivative of general formula (VII-3) is converted to a Grignard reagent (VIII-3) according to the method described in J. Org. Chem., 20, 1159 (1955) or the like, and the Grignard reagent (VIII-3) is allowed to react with sulfuryl chloride to obtain a sulfonyl halide derivative of general formula (IX). Thereafter, the sulfamoylamine of general formula (IV) can be produced in the same manner as in (A).

(D) General Formula (VII-4)→General Formula (IV)

A sulfenamide derivative of general formula (VIII-4) is obtained from a sulfenic acid derivative of general formula (VII-4) and an amine derivative of general formula (X) according to the method described in J. Am. Chem. Soc., 57, 2172 (1935), Chem. Lett, 1976, 149 or the like. The sulfenamide derivative is converted to a sulfonamide derivative of general formula (IV-1) according to the method described in J. Org. Chem., 31, 2357 (1966) or the like. Thereafter, the sulfamoylamine of general formula (IV) can be produced by subjecting the sulfonamide derivative to deprotection in the same manner as in (A).

(E) General Formula (VII-5)→General Formula (IV)

As the sulfamoylamine of general formula (IV), a sulfamoylamine in which each of R¹ and R² is a hydrogen atom can be produced by obtaining a sulfonamide derivative of general formula (IV-1) from a sulfenate derivative of general formula (VII-5) and hydroxylamine-O-sulfonic acid (XI) according to the method described in Synthesis, 1985, 1032, and then subjecting the sulfonamide derivative to deprotection in the same manner as in (A). Such a sulfamoylamine of general formula (IV) can be produced also by obtaining a sulfonamide derivative of general formula (IV-1) from a sulfenate derivative of general formula (VII-5) and a N-halo-substituted amine of general formula (XII) according to the method described in J. Org. Chem., 46, 5077 (1981), and then subjecting the sulfonamide derivative to deprotection in the same manner as in (A).

Typical compounds as the sulfonamide derivative of general formula (I) are listed below in Table 1 and Table 2 but they are not intended in any way to limit the scope of the present invention. In the following tables, “n” is a prefix for “normal”, “s” is a prefix for “secondary”, “t” is a prefix for “tertiary”, “i” is a prefix for “iso”, “c” is a prefix for “cyclo”, and “Me” indicates a methyl group, “Et” an ethyl group, “Pr” a propyl group, “Bu” a butyl group, “Pen” a pentyl group, “Hex” a hexyl group, “Ph” a phenyl group, “Py” a pyridyl group, and “C*” an asymmetric carbon atom. In addition, “J¹”, “J²” and “J³” indicate the following substituents.

TABLE 1 General formula (I-1) (I-1)

Physical property: Melting No. —A—SO₂NR¹R² Xm Yn point ° C. 1-1 CHMeCH₂SO₂NH₂ 3-I 2-Me-4-CF(CF₃)₂ 217-219 1-2 CHMeCH₂SO₂NHMe 3-I 2-Me-4-CF(CF₃)₂ 186-188 1-3 CHMeCH₂SO₂NMe₂ 3-I 2-Me-4-CF(CF₃)₂ 122-125 1-4 CHMeCH₂SO₂NHEt 3-I 2-Me-4-CF(CF₃)₂ 170-172 1-5 CHMeCH₂SO₂N(Me)Et 3-I 2-Me-4-CF(CF₃)₂ 1-6 CHMeCH₂SO₂NEt₂ 3-I 2-Me-4-CF(CF₃)₂ 116 1-7 CHMeCH₂SO₂NH-n-Pr 3-I 2-Me-4-CF(CF₃)₂ 147-150 1-8 CHMeCH₂SO₂NH-i-Pr 3-I 2-Me-4-CF(CF₃)₂ 204-206 1-9 CHMeCH₂SO₂NH-c-Pr 3-I 2-Me-4-CF(CF₃)₂ 1-10 CHMeCH₂SO₂N(n-Pr)₂ 3-I 2-Me-4-CF(CF₃)₂ 1-11 CHMeCH₂SO₂N(i-Pr)₂ 3-I 2-Me-4-CF(CF₃)₂ 1-12 CHMeCH₂SO₂NH-n-Bu 3-I 2-Me-4-CF(CF₃)₂ 178-181 1-13 CHMeCH₂SO₂NH-s-Bu 3-I 2-Me-4-CF(CF₃)₂ 1-14 CHMeCH₂SO₂NH-t-Bu 3-I 2-Me-4-CF(CF₃)₂ 195-197 1-15 CHMeCH₂SO₂NH-i-Bu 3-I 2-Me-4-CF(CF₃)₂ 1-16 CHMeCH₂SO₂NH-c-Bu 3-I 2-Me-4-CF(CF₃)₂ 1-17 CHMeCH₂SO₂NH-c-Pen 3-I 2-Me-4-CF(CF₃)₂ 1-18 CHMeCH₂SO₂NH-c-Hex 3-I 2-Me-4-CF(CF₃)₂ 1-19 CHMeCH₂SO₂NHCH₂-c-Pr 3-I 2-Me-4-CF(CF₃)₂ 1-20 CHMeCH₂SO₂NHCH₂CH═CH₂ 3-I 2-Me-4-CF(CF₃)₂ 109-113 1-21 CHMeCH₂SO₂NHCH₂C≡CH 3-I 2-Me-4-CF(CF₃)₂ 111-113 1-22 CHMeCH₂SO₂NHCH₂Ph 3-I 2-Me-4-CF(CF₃)₂ 200-202 1-23 CHMeCH₂SO₂NHCH₂-(2-F-Ph) 3-I 2-Me-4-CF(CF₃)₂ 195-198 1-24 CHMeCH₂SO₂NHCH₂-(2-Cl-Ph) 3-I 2-Me-4-CF(CF₃)₂ 193-196 1-25 CHMeCH₂SO₂NHCH₂-(2-Br-Ph) 3-I 2-Me-4-CF(CF₃)₂ 189-192 1-26 CHMeCH₂SO₂NHCH₂-(2-Me-Ph) 3-I 2-Me-4-CF(CF₃)₂ 1-27 CHMeCH₂SO₂NHCH₂-(2-OMe-Ph) 3-I 2-Me-4-CF(CF₃)₂ 180-183 1-28 CHMeCH₂SO₂NHCH₂-(2-NO₂-Ph) 3-I 2-Me-4-CF(CF₃)₂ 173-177 1-29 CHMeCH₂SO₂NHCH₂-(3-OMe-Ph) 3-I 2-Me-4-CF(CF₃)₂ 196-198 1-30 CHMeCH₂SO₂NHCH₂-(3-NO₂-Ph) 3-I 2-Me-4-CF(CF₃)₂ 155-160 1-31 CHMeCH₂SO₂NHCH₂-(3-CN-Ph) 3-I 2-Me-4-CF(CF₃)₂ 147-150 1-32 CHMeCH₂SO₂NHCH₂-(2,6-(OMe)₂-Ph) 3-I 2-Me-4-CF(CF₃)₂ 210-213 1-33 CHMeCH₂SO₂NHCH₂-(4-Cl-Ph) 3-I 2-Me-4-CF(CF₃)₂ 1-34 CHMeCH₂SO₂NHCH₂-(4-Me-Ph) 3-I 2-Me-4-CF(CF₃)₂ 1-35 CHMeCH₂SO₂NHCH₂-(4-MeO-Ph) 3-I 2-Me-4-CF(CF₃)₂ 176-179 1-36 CHMeCH₂SO₂NHCH₂-(4-NO₂-Ph) 3-I 2-Me-4-CF(CF₃)₂ 185-187 1-37 CHMeCH₂SO₂NHCH₂-(4-CN-Ph) 3-I 2-Me-4-CF(CF₃)₂ 169-171 1-38 CHMeCH₂SO₂NHCH₂-(4-SCF₃-Ph) 3-I 2-Me-4-CF(CF₃)₂ 201-204 1-39 CHMeCH₂SO₂NHCH₂-2-Py 3-I 2-Me-4-CF(CF₃)₂ 228-231 1-40 CHMeCH₂SO₂NHCH₂-3-Py 3-I 2-Me-4-CF(CF₃)₂ 144-147 1-41 CHMeCH₂SO₂NHCH₂-4-Py 3-I 2-Me-4-CF(CF₃)₂ 166-168 1-42 CHMeCH₂SO₂N(Me)CH₂Ph 3-I 2-Me-4-CF(CF₃)₂ 186-189 1-43 CHMeCH₂SO₂N(Et)CH₂Ph 3-I 2-Me-4-CF(CF₃)₂ 184-186 1-44 CHCH₂SO₂NHCH(Me)Ph 3-I 2-Me-4-CF(CF₃)₂ 173-175 1-45 CHMeCH₂SO₂NHCH(Me)Ph 3-I 2-Me-4-CF(CF₃)₂ 168-170 R-enantiomer 1-46 CHMeCH₂SO₂NHC*H(Me)Ph 3-I 2-Me-4-CF(CF₃)₂ 159-161 S-enantiomer 1-47 CHMeCH₂SO₂NHCH₂CH₂Ph 3-I 2-Me-4-CF(CF₃)₂ 203-206 1-48 CHMeCH₂SO₂NHC(Me)2CH₂Ph 3-I 2-Me-4-CF(CF₃)₂ 197-198 1-49 CHMeCH₂SO₂N(CH₂)₂ 3-I 2-Me-4-CF(CF₃)₂ 1-50 CHMeCH₂SO₂N(CH₂)₃ 3-I 2-Me-4-CF(CF₃)₂ 1-51 CHMeCH₂SO₂N(CH₂)₄ 3-I 2-Me-4-CF(CF₃)₂ 1-52 CHMeCH₂SO₂N(CH₂)₅ 3-I 2-Me-4-CF(CF₃)₂ 1-53 CHMeCH₂SO₂N(CH₂)₆ 3-I 2-Me-4-CF(CF₃)₂ 1-54 CHMeCH₂SO₂N(CH₂CH₂)₂O 3-I 2-Me-4-CF(CF₃)₂ 204-207 1-55 CHMeCH₂SO₂N(CH₂CH₂)₂S 3-I 2-Me-4-CF(CF₃)₂ 191-194 1-56 CHMeCH₂SO₂N(CH₂CH₂)₂SO 3-I 2-Me-4-CF(CF₃)₂ 195-198 1-57 CHMeCH₂SO₂N(CH₂CH₂)₂SO₂ 3-I 2-Me-4-CF(CF₃)₂ 237-240 1-58 OMe2CH₂SO₂N(CH₂CH₂)₂S 3-I 2-Me-4-CF(CF₃)₂ 164-165 1-59 OMe2CH₂SO₂N(CH₂CH₂)₂SO 3-I 2-Me-4-CF(CF₃)₂ 167-168 1-60 OMe2CH₂SO₂N(CH₂CH₂)₂SO₂ 3-I 2-Me-4-CF(CF₃)₂ 166-167 1-61 OMe2CH₂SO₂J¹ 3-I 2-Me-4-CF(CF₃)₂ 207-208 1-62 OMe2CH₂SO₂J² 3-I 2-Me-4-CF(CF₃)₂ Amorphous 1-63 OMe2CH₂SO₂J³ 3-I 2-Me-4-CF(CF₃)₂ 157-159 1-64 CHMeCH₂SO₂N(CH₂CH₂)₂NH 3-I 2-Me-4-CF(CF₃)₂ 1-65 CHMeCH₂SO₂N(CH₂CH₂)₂NMe 3-I 2-Me-4-CF(CF₃)₂ 1-66 CHMeCH₂SO₂N(CH₂CH₂)₂NOOMe 3-I 2-Me-4-CF(CF₃)₂ 196-198 1-67 CHMeCH₂SO₂N(CH₂CH₂)₂C═O 3-I 2-Me-4-CF(CF₃)₂ 209-211 1-68 CHMeCH₂SO₂NHCH₂CF₃ 3-I 2-Me-4-CF(CF₃)₂ 1-69 CHMeCH₂SO₂NHCH(Me)CF₃ 3-I 2-Me-4-CF(CF₃)₂ 1-70 CHMeCH₂SO₂NHCH₂CH═OCl₂ 3-I 2-Me-4-CF(CF₃)₂ 1-71 CHMeCH₂SO₂NH(CH₂)₂Cl 3-I 2-Me-4-CF(CF₃)₂ 90-95 1-72 CHMeCH₂SO₂NH(CH₂)₂OH 3-I 2-Me-4-CF(CF₃)₂ 171-174 1-73 CHMeCH₂SO₂NH(CH₂)₂OMe 3-I 2-Me-4-CF(CF₃)₂ 142-144 1-74 CHMeCH₂SO₂NHCHMeCH₂OMe 3-I 2-Me-4-CF(CF₃)₂ 1-75 CHMeCH₂SO₂NH(CH₂)₂SMe 3-I 2-Me-4-CF(CF₃)₂ 156-158 1-76 CHMeCH₂SO₂NH(CH₂)₂SOMe 3-I 2-Me-4-CF(CF₃)₂ 132-134 1-77 CHMeCH₂SO₂NH(CH₂)₂SO₂Me 3-I 2-Me-4-CF(CF₃)₂ 186-189 1-78 OMe₂CH₂SO₂NH(CH₂)₂OH 3-I 2-Me-4-CF(CF₃)₂ 150-151 1-79 OMe₂CH₂SO₂NH(CH₂)₂OMe 3-I 2-Me-4-CF(CF₃)₂ 167-168 1-80 OMe₂CH₂SO₂NH(CH₂)₂OOOMe 3-I 2-Me-4-CF(CF₃)₂ 181-182 1-81 OMe₂CH₂SO₂NH(CH₂)₂SMe 3-I 2-Me-4-CF(CF₃)₂ 161-162 1-82 OMe₂CH₂SO₂NH(CH₂)₂SOMe 3-I 2-Me-4-CF(CF₃)₂ 154-155 1-83 OMe₂CH₂SO₂NH(CH₂)₂SO₂Me 3-I 2-Me-4-CF(CF₃)₂ 151-152 1-84 OMe₂CH₂SO₂NH(CH₂)₂SEt 3-I 2-Me-4-CF(CF₃)₂ 166-167 1-85 OMe₂CH₂SO₂NH(CH₂)₂SOEt 3-I 2-Me-4-CF(CF₃)₂ 144-145 1-86 OMe₂CH₂SO₂NH(CH₂)₂SO2Et 3-I 2-Me-4-CF(CF₃)₂ 168-169 1-87 OMe₂CH₂SO₂NH(CH₂)₂SPh 3-I 2-Me-4-CF(CF₃)₂ 155-156 1-88 OMe₂CH₂SO₂NH(CH₂)₂SOPh 3-I 2-Me-4-CF(CF₃)₂ 151-153 1-89 OMe₂CH₂SO₂NH(CH₂)₂SO₂Ph 3-I 2-Me-4-CF(CF₃)₂ 170-172 1-90 OMe₂CH₂SO₂NH(CH₂)₂NMe₂ 3-I 2-Me-4-CF(CF₃)₂ 1-91 CHMeCH₂SO₂NHCHMeCH₂SMe 3-I 2-Me-4-CF(CF₃)₂ 190-193 1-92 CHMeCH₂SO₂NHCHMeCH₂SOMe 3-I 2-Me-4-CF(CF₃)₂ 130-133 1-93 CHMeCH₂SO₂NHCHMeCH₂SO₂Me 3-I 2-Me-4-CF(CF₃)₂ 150-154 1-94 CHMeCH₂SO₂NOMe₂CH₂SMe 3-I 2-Me-4-CF(CF₃)₂ 157-160 1-95 CHMeCH₂SO₂NH(CH₂)₃OMe 3-I 2-Me-4-CF(CF₃)₂ 1-96 OMe₂CH₂SO₂NH(CH₂)₃SMe 3-I 2-Me-4-CF(CF₃)₂ 1-97 OMe₂CH₂SO₂NH(CH₂)₃SOMe 3-I 2-Me-4-CF(CF₃)₂ 1-98 OMe₂CH₂SO₂NH(CH₂)₃SO₂Me 3-I 2-Me-4-CF(CF₃)₂ 1-99 CHMeCH₂SO₂NHCH₂CN 3-I 2-Me-4-CF(CF₃)₂ 1-100 CHMeCH₂SO₂NHCH₂CO₂Me 3-I 2-Me-4-CF(CF₃)₂ 1-101 CHMeCH₂SO₂NHCH₂CO₂Et 3-I 2-Me-4-CF(CF₃)₂ 1-102 CHMeCH₂SO₂NHCHMeCO₂Me 3-I 2-Me-4-CF(CF₃)₂ 1-103 CHMeCH₂SO₂NHCHMeCONH₂ 3-I 2-Me-4-CF(CF₃)₂ 228-230 1-104 CHMeCH₂SO₂NHCHMeCONHEt 3-I 2-Me-4-CF(CF₃)₂ 176-177 1-105 CHMeCH₂SO₂NHCH₂CONEt₂ 3-I 2-Me-4-CF(CF₃)₂ 172-174 1-106 CHMeCH₂SO₂NHPh 3-I 2-Me-4-CF(CF₃)₂ 232-234 1-107 CHMeCH₂SO₂NH(2-F-Ph) 3-I 2-Me-4-CF(CF₃)₂ 211-212 1-108 CHMeCH₂SO₂NH(2-MeO-Ph) 3-I 2-Me-4-CF(CF₃)₂ 101-106 1-109 CHMeCH₂SO₂NH(3-F-Ph) 3-I 2-Me-4-CF(CF₃)₂ 235-236 1-110 CHMeCH₂SO₂NH(4-F-Ph) 3-I 2-Me-4-CF(CF₃)₂ 228-233 1-111 CHMeCH₂SO₂NH(4-MeO-Ph) 3-I 2-Me-4-CF(CF₃)₂ 143-147 1-112 CHMeCH₂SO₂NH(4-MeS-Ph) 3-I 2-Me-4-CF(CF₃)₂ 165-170 1-113 CHMeCH₂SO₂NH-2-Py 3-I 2-Me-4-CF(CF₃)₂ 1-114 CHMeCH₂SO₂NH-3-Py 3-I 2-Me-4-CF(CF₃)₂ 1-115 CHMeCH₂SO₂NHOH 3-I 2-Me-4-CF(CF₃)₂ 1-116 CHMeCH₂SO₂NHOMe 3-I 2-Me-4-CF(CF₃)₂ 200-205 1-117 CHMeCH₂SO₂NMeOMe 3-I 2-Me-4-CF(CF₃)₂ 1-118 CHMeCH₂SO₂NHNH₂ 3-I 2-Me-4-CF(CF₃)₂ 1-119 CHMeCH₂SO₂NMeNH₂ 3-I 2-Me-4-CF(CF₃)₂ 1-120 CHMeCH₂SO₂NMeNHMe 3-I 2-Me-4-CF(CF₃)₂ 1-121 CHMeCH₂SO₂NHMe₂ 3-I 2-Me-4-CF(CF₃)₂ 161-166 1-122 CHMeCH₂SO₂NHNHPh 3-I 2-Me-4-CF(CF₃)₂ 1-123 CHMeCH₂SO₂NHNHOOMe 3-I 2-Me-4-CF(CF₃)₂ 1-124 CHMeCH₂SO₂NHNHOOPh 3-I 2-Me-4-CF(CF₃)₂ 1-125 CHMeCH₂SO₂NHN═OMe₂ 3-I 2-Me-4-CF(CF₃)₂ 1-126 CHMeCH₂SO₂NHN═CHPh 3-I 2-Me-4-CF(CF₃)₂ 1-127 CHMeCH₂SO₂NHN═C(Me)Ph 3-I 2-Me-4-CF(CF₃)₂ 1-128 CHMeCH₂SO₂N═CHMe 3-I 2-Me-4-CF(CF₃)₂ 1-129 CHMeCH₂SO₂N═CHEt 3-I 2-Me-4-CF(CF₃)₂ 1-130 CHMeCH₂SO₂N═CH-i-Pr 3-I 2-Me-4-CF(CF₃)₂ 1-131 CHMeCH₂SO₂N═CHPh 3-I 2-Me-4-CF(CF₃)₂ 1-132 CHMeCH₂SO₂N═CHNHMe 3-I 2-Me-4-CF(CF₃)₂ 1-133 CHMeCH₂SO₂N═CHNMe₂ 3-I 2-Me-4-CF(CF₃)₂ 1-134 CHMeCH₂SO₂N═CHNEt₂ 3-I 2-Me-4-CF(CF₃)₂ 1-135 C*HMeCH₂SO₂NH₂ 3-I 2-Me-4-CF(CF₃)₂ R-enantiomer 1-136 C*HMeCH₂SO₂NH₂ 3-I 2-Me-4-CF(CF₃)₂ S-enantiomer 1-137 C*HMeCH₂SO₂NHMe 3-I 2-Me-4-CF(CF₃)₂ R-enantiomer 1-138 C*HMeCH₂SO₂NHMe 3-I 2-Me-4-CF(CF₃)₂ S-enantiomer 1-139 C*HMeCH₂SO₂NMe₂ 3-I 2-Me-4-CF(CF₃)₂ R-enantiomer 1-140 C*HMeCH₂SO₂NMe₂ 3-I 2-Me-4-CF(CF₃)₂ S-enantiomer 1-141 C*HMeCH₂SO₂NHEt 3-I 2-Me-4-CF(CF₃)₂ R-enantiomer 1-142 C*HMeCH₂SO₂NHEt 3-I 2-Me-4-CF(CF₃)₂ 105-107 S-enantiomer 1-143 C*HMeCH₂SO₂NEt₂ 2-Me-4-CF(CF₃)₂ R-enantiomer 1-144 C*HMeCH₂SO₂NEt₂ 3-I 2-Me-4-CF(CF₃)₂ 159-163 S-enantiomer 1-145 C*HMeCH₂SO₂NHCH₂Ph 3-I 2-Me-4-CF(CF₃)₂ R-enantiomer 1-146 C*HMeCH₂SO₂NHCH₂Ph 3-I 2-Me-4-CF(CF₃)₂ 158-159 S-enantiomer 1-147 C*HMeCH₂SO₂NHC*HMeCH₂SMe 3-I 2-Me-4-CF(CF₃)₂ Amorphous S,S-enantiomer 1-148 C*HMeCH₂SO₂NHC*HMeCH₂SOMe 3-I 2-Me-4-CF(CF₃)₂ 115-120 S,S-enantiomer 1-149 C*HMeCH₂SO₂NHC*HMeCH₂SO₂Me 3-I 2-Me-4-CF(CF₃)₂ Amorphous S,S-enantiomer 1-150 CHMeSO₂NH₂ 3-I 2-Me-4-CF(CF₃)₂ 1-151 CHMeSO₂NHMe 3-I 2-Me-4-CF(CF₃)₂ 1-152 CHMeSO₂NMe₂ 3-I 2-Me-4-CF(CF₃)₂ 1-153 CHMeSO₂NHEt 3-I 2-Me-4-CF(CF₃)₂ 1-154 CHMeSO₂NEt₂ 3-I 2-Me-4-CF(CF₃)₂ 1-155 CHMe(CH₂)₂SO₂NH₂ 3-I 2-Me-4-CF(CF₃)₂ 1-156 CHMe(CH₂)₂SO₂NHMe 3-I 2-Me-4-CF(CF₃)₂ 1-157 CHMe(CH₂)₂SO₂NMe₂ 3-I 2-Me-4-CF(CF₃)₂ 1-158 CHMe(CH₂)₂SO₂NHEt 3-I 2-Me-4-CF(CF₃)₂ 1-159 CHMe(CH₂)₂SO₂NEt₂ 3-I 2-Me-4-CF(CF₃)₂ 1-160 CHMe(CH₂)₂SO₂NH₂ 3-I 2-Me-4-CF(CF₃)₂ S-enantiomer 1-161 C*HMe(CH₂)₂SO₂NHMe 3-I 2-Me-4-CF(CF₃)₂ S-enantiomer 1-162 C*HMe(CH₂)₂SO₂NMe₂ 3-I 2-Me-4-CF(CF₃)₂ S-enantiomer 1-163 C*HMe(CH₂)₂SO₂NHEt 3-I 2-Me-4-CF(CF₃)₂ S-enantiomer 1-164 C*HMe(CH₂)₂SO₂NEt₂ 3-I 2-Me-4-CF(CF₃)₂ S-enantiomer 1-165 CHMe(CH₂)3SO₂NH₂ 3-I 2-Me-4-CF(CF₃)₂ 1-166 CHMe(CH₂)3SO₂NHMe 3-I 2-Me-4-CF(CF₃)₂ 1-167 CHMe(CH₂)3SO₂NMe₂ 3-I 2-Me-4-CF(CF₃)₂ 1-168 CHMe(CH₂)3SO₂NHEt 3-I 2-Me-4-CF(CF₃)₂ 1-169 CHMe(CH₂)3SO₂NEt₂ 3-I 2-Me-4-CF(CF₃)₂ 1-170 CHMe(CH₂)4SO₂NH₂ 3-I 2-Me-4-CF(CF₃)₂ 1-171 CHMe(CH₂)4SO₂NHMe 3-I 2-Me-4-CF(CF₃)₂ 1-172 CHMe(CH₂)4SO₂NMe₂ 3-I 2-Me-4-CF(CF₃)₂ 1-173 CHMe(CH₂)4SO₂NHEt 3-I 2-Me-4-CF(CF₃)₂ 1-174 CHMe(CH₂)4SO₂NEt₂ 3-I 2-Me-4-CF(CF₃)₂ 1-175 OMe₂CH₂SO₂NH₂ 3-I 2-Me-4-CF(CF₃)₂ Amorphous 1-176 OMe₂CH₂SO₂NHMe 3-I 2-Me-4-CF(CF₃)₂ Amorphous 1-177 OMe₂CH₂SO₂NMe₂ 3-I 2-Me-4-CF(CF₃)₂ 151-152 1-178 OMe₂CH₂SO₂NHEt 3-I 2-Me-4-CF(CF₃)₂ Amorphous 1-179 OMe₂CH₂SO₂NEt₂ 3-I 2-Me-4-CF(CF₃)₂ Amorphous 1-180 OMe₂CH₂SO₂NH-n-Bu 3-I 2-Me-4-CF(CF₃)₂ 185-186 1-181 OMe₂CH₂SO₂N(CH₂)₄ 3-I 2-Me-4-CF(CF₃)₂ 129-130 1-182 OMe₂CH₂SO₂NHCH₂CH═CH₂ 3-I 2-Me-4-CF(CF₃)₂ 1-183 OMe₂CH₂SO₂NHCH₂C═CH 3-I 2-Me-4-CF(CF₃)₂ 1-184 OMe₂CH₂SO₂NHCH₂Ph 3-I 2-Me-4-CF(CF₃)₂ 152-153 1-185 OMe₂CH₂SO₂NHPh 3-I 2-Me-4-CF(CF₃)₂ 1-186 OMe₂CH₂SO₂NH-2-Py 3-I 2-Me-4-CF(CF₃)₂ 1-187 OMe₂SO₂NH₂ 3-I 2-Me-4-CF(CF₃)₂ 1-188 OMe₂SO₂NHMe 3-I 2-Me-4-CF(CF₃)₂ 1-189 OMe₂SO₂NMe₂ 3-I 2-Me-4-CF(CF₃)₂ 1-190 OMe₂SO₂NHEt 3-I 2-Me-4-CF(CF₃)₂ 1-191 OMe₂SO₂NEt₂ 3-I 2-Me-4-CF(CF₃)₂ 1-192 OMe₂(CH₂)₂SO₂NH₂ 3-I 2-Me-4-CF(CF₃)₂ 1-193 OMe₂(CH₂)₂SO₂NHMe 3-I 2-Me-4-CF(CF₃)₂ 1-194 OMe₂(CH₂)₂SO₂NMe₂ 3-I 2-Me-4-CF(CF₃)₂ 1-195 OMe₂(CH₂)₂SO₂NHEt 3-I 2-Me-4-CF(CF₃)₂ 1-196 OMe₂(CH₂)₂SO₂NEt₂ 3-I 2-Me-4-CF(CF₃)₂ 1-197 OMe₂(CH₂)₃SO₂NH₂ 3-I 2-Me-4-CF(CF₃)₂ 1-198 OMe₂(CH₂)₃SO₂NHMe 3-I 2-Me-4-CF(CF₃)₂ 1-199 OMe₂(CH₂)₃SO₂NMe₂ 3-I 2-Me-4-CF(CF₃)₂ 1-200 OMe₂(CH₂)₃SO₂NHEt 3-I 2-Me-4-CF(CF₃)₂ 185-186 1-201 OMe₂(CH₂)₃SO₂NEt₂ 3-I 2-Me-4-CF(CF₃)₂ 142-145 1-202 OMe₂(CH₂)₄SO₂NH₂ 3-I 2-Me-4-CF(CF₃)₂ 1-203 OMe₂(CH₂)₄SO₂NHMe 3-I 2-Me-4-CF(CF₃)₂ 1-204 OMe₂(CH₂)₄SO₂NMe₂ 3-I 2-Me-4-CF(CF₃)₂ 1-205 OMe₂(CH₂)₄SO₂NHEt 3-I 2-Me-4-CF(CF₃)₂ 1-206 OMe₂(CH₂)₄SO₂NEt₂ 3-I 2-Me-4-CF(CF₃)₂ 1-207 CHMeCH₂SO₂NHEt H 2-Me-4-CF(CF₃)₂ 120-121 1-208 OMe₂CH₂SO₂NEt₂ H 2-Me-4-CF(CF₃)₂ 93-94 1-209 CHMeCH₂SO₂NHEt 3-F 2-Me-4-CF(CF₃)₂ 1-210 CHMeCH₂SO₂NHEt 3-Cl 2-Me-4-CF(CF₃)₂ 1-211 CHMeCH₂SO₂NEt₂ 3-Cl 2-Me-4-CF(CF₃)₂ 103-108 1-212 CHMeCH₂SO₂NHEt 3-Br 2-Me-4-CF(CF₃)₂ 136-138 1-213 CHMeCH₂SO₂NMe₂ 3-Br 2-Me-4-CF(CF₃)₂ 107-110 1-214 CHMeCH₂SO₂NEt₂ 3-Br 2-Me-4-CF(CF₃)₂ 112-115 1-215 CHMeCH₂SO₂NH-n-Pr 3-Br 2-Me-4-CF(CF₃)₂ 159-161 1-216 CHMeCH₂SO₂NH-i-Pr 3-Br 2-Me-4-CF(CF₃)₂ 185-187 1-217 CHMeCH₂SO₂NH-n-Bu 3-Br 2-Me-4-CF(CF₃)₂ 179-181 1-218 CHMeCH₂SO₂NHCH₂Ph 3-Br 2-Me-4-CF(CF₃)₂ 139-141 1-219 OMe₂CH₂SO₂NEt₂ 3-Br 2-Me-4-CF(CF₃)₂ 169-170 1-220 CHMeCH₂SO₂NHEt 3,4-Cl₂ 2-Me-4-CF(CF₃)₂ 1-221 CHMeCH₂SO₂NHEt 3,4-Br₂ 2-Me-4-CF(CF₃)₂ 1-222 CHMeCH₂SO₂NHEt 4-Cl 2-Me-4-CF(CF₃)₂ 1-223 CHMeCH₂SO₂NHEt 4-Br 2-Me-4-CF(CF₃)₂ 1-224 CHMeCH₂SO₂NHEt 4-I 2-Me-4-CF(CF₃)₂ 1-225 CHMeCH₂SO₂NHEt 3-NO₂ 2-Me-4-CF(CF₃)₂ 1-226 CHMeCH₂SO₂NHEt 3-NH₂ 2-Me-4-CF(CF₃)₂ 1-227 CHMeCH₂SO₂NHEt 3-N(CH₃)₂ 2-Me-4-CF(CF₃)₂ 1-228 CHMeCH₂SO₂NHEt 3-NHCOCH₃ 2-Me-4-CF(CF₃)₂ 1-229 CHMeCH₂SO₂NHEt 3-NHCOCF₃ 2-Me-4-CF(CF₃)₂ 1-230 CHMeCH₂SO₂NHEt 3-NHSO₂CH₃ 2-Me-4-CF(CF₃)₂ 1-231 CHMeCH₂SO₂NHEt 3-NHSO₂CF₃ 2-Me-4-CF(CF₃)₂ 1-232 CHMeCH₂SO₂NHEt 3-CH₃ 2-Me-4-CF(CF₃)₂ 1-233 CHMeCH₂SO₂NHEt 3-CF₃ 2-Me-4-CF(CF₃)₂ 1-234 CHMeCH₂SO₂NHEt 3-OCH₃ 2-Me-4-CF(CF₃)₂ 1-235 CHMeCH₂SO₂NHEt 3-OCF₃ 2-Me-4-CF(CF₃)₂ 1-236 CHMeCH₂SO₂NHEt 3-OCOCH₃ 2-Me-4-CF(CF₃)₂ 1-237 CHMeCH₂SO₂NHEt 3-OCOCF₃ 2-Me-4-CF(CF₃)₂ 1-238 CHMeCH₂SO₂NHEt 3-SCH₃ 2-Me-4-CF(CF₃)₂ 1-239 CHMeCH₂SO₂NHEt 3-SOCH₃ 2-Me-4-CF(CF₃)₂ 1-240 CHMeCH₂SO₂NHEt 3-SO₂CH₃ 2-Me-4-CF(CF₃)₂ 1-241 CHMeCH₂SO₂NHEt 3-SCF₃ 2-Me-4-CF(CF₃)₂ 1-242 CHMeCH₂SO₂NHEt 3-SOCF₃ 2-Me-4-CF(CF₃)₂ 1-243 CHMeCH₂SO₂NHEt 3-SO₂CF₃ 2-Me-4-CF(CF₃)₂ 1-244 CHMeCH₂SO₂NHEt 3-OSO₂CH₃ 2-Me-4-CF(CF₃)₂ 1-245 CHMeCH₂SO₂NHEt 3-OSO₂CF₃ 2-Me-4-CF(CF₃)₂ 1-246 CHMeCH₂SO₂NHEt 3-C≡CH 2-Me-4-CF(CF₃)₂ 1-247 CHMeCH₂SO₂NHEt 3-C≡CCF₃ 2-Me-4-CF(CF₃)₂ 1-248 CHMeCH₂SO₂NHEt 3-CN 2-Me-4-CF(CF₃)₂ 1-249 CHMeCH₂SO₂NHEt 3-CHCHCHCH-4 2-Me-4-CF(CF₃)₂ 1-250 CHMeCH₂SO₂NHEt 3-OCF₂O-4 2-Me-4-CF(CF₃)₂ 1-251 CHMeCH₂SO₂NHEt 3-OCF₂CF₂O-4 2-Me-4-CF(CF₃)₂ 1-252 CHMeCH₂SO₂NHEt 3-I 2-Me-4-F 1-253 CHMeCH₂SO₂NHEt 3-I 2-Me-4-Cl 1-254 CHMeCH₂SO₂NHEt 3-I 2-Me-4-Br 1-255 CHMeCH₂SO₂NHEt 3-I 2-Me-4-I 1-256 CHMeCH₂SO₂NHEt 3-I 2-Me-3-F-4-Cl 1-257 CHMeCH₂SO₂NHEt 3-I 2-Me-3-Cl-4-F 1-258 CHMeCH₂SO₂NHEt 3-I 2-Me-3,4-Cl₂ 1-259 CHMeCH₂SO₂NHEt 3-I 2-Me-3-Cl-4-Br 1-260 CHMeCH₂SO₂NHEt 3-I 2-Me-3-C1-4-I 1-261 CHMeCH₂SO₂NHEt 3-I 2,4-Cl₂ 1-262 CHMeCH₂SO₂NHEt 3-I 2-Cl-4-Br 1-263 CHMeCH₂SO₂NHEt 3-I 2-Cl-4-I 1-264 CHMeCH₂SO₂NHEt 3-I 2,4-Br₂ 1-265 CHMeCH₂SO₂NHEt 3-I 2-Br-4-I 1-266 CHMeCH₂SO₂NHEt 3-I 2,3,4-Cl₃ Amorphous 1-267 CHMeCH₂SO₂NEt₂ 3-I 2,3,4-Cl₃ 114-118 1-268 OMe₂CH₂SO₂NEt₂ 3-I 2,3,4-Cl₃ 164-166 1-269 CHMeCH₂SO₂NHEt 3-I 2,3-Cl₂-4-F 1-270 CHMeCH₂SO₂NHEt 3-I 2,3-Cl₂-4-Br 1-271 CHMeCH₂SO₂NHEt 3-I 2,3-Cl₂-4-I 1-272 CHMeCH₂SO₂NHEt 3-I 2,4-Cl₂-3-Br 1-273 CHMeCH₂SO₂NHEt 3-I 2,4-Cl₂-3-F 1-274 CHMeCH₂SO₂NHEt 3-I 2-Me-4-OCHF₂ 1-275 CHMeCH₂SO₂NHEt 3-I 2-Me-4-OCF₃ 181-182 1-276 CHMeCH₂SO₂NEt₂ 3-I 2-Me-4-OCF₃ Amorphous 1-277 OMe₂CH₂SO₂NEt₂ 3-I 2-Me-4-OCF₃ Amorphous 1-278 CHMeCH₂SO₂NHEt 3-I 2-Me-4-OCF₂CF₃ 1-279 CHMeCH₂SO₂NHEt 3-I 2-Me-4-OCF₂CHF₂ 1-280 CHMeCH₂SO₂NHEt 3-I 2-Me-4-OCF₂CHFCF₃ 1-281 CHMeCH₂SO₂NHEt 3-I 2-Me-4-OCF₂CHFOCF₃ 1-282 CHMeCH₂SO₂NHEt 3-I 2-Me-4-OCF₂CHFOC₃F₇-n 1-283 CHMeCH₂SO₂NHEt 3-I 2-Cl-4-OCHF₂ 1-284 CHMeCH₂SO₂NHEt 3-I 2-Cl-4-OCF₃ 1-285 CHMeCH₂SO₂NEt₂ 3-I 2-Cl-4-OCF₃ 100-103 1-286 OMe₂CH₂SO₂NEt₂ 3-I 2-Cl-4-OCF₃ 141-142 1-287 CHMeCH₂SO₂NHEt 3-I 2-Cl-4-OCF2CF₃ 1-288 CHMeCH₂SO₂NHEt 3-I 2-Cl-4-OCF₂CHF₂ 1-289 CHMeCH₂SO₂NHEt 3-I 2-Cl-4-OCF₂CHFCF₃ 1-290 CHMeCH₂SO₂NHEt 3-I 2-Cl-4-OCF₂CHFOCF₃ 1-291 CHMeCH₂SO₂NHEt 3-I 2-Cl-4-OCF₂CHFOC₃F₇-n 1-292 CHMeCH₂SO₂NHEt 3-I 2,3-Cl₂-4-OCF₃ 1-293 CHMeCH₂SO₂NHEt 3-I 2,3-Cl₂-4-OCF₂CHF₂ 1-294 CHMeCH₂SO₂NHEt 3-I 2,3-Cl₂-4-OCF₂CHFCF₃ 1-295 CHMeCH₂SO₂NHEt 3-I 2,3-Cl₂-4-OCF₂CHFOCF₃ 1-296 CHMeCH₂SO₂NHEt 3-I 2,3-Cl₂-4-OCF₂CHFOC₃F₇-n 1-297 CHMeCH₂SO₂NHEt 3-I 4-CF₂CF₂CF₃ 1-298 CHMeCH₂SO₂NHEt 3-I 4-CF(CF₃)₂ 1-299 CHMeCH₂SO₂NHEt 3-I 2-Me-4-CF₃ 1-300 CHMeCH₂SO₂NHEt 3-I 2-Me-4-CF₂CF₃ 1-301 CHMeCH₂SO₂NEt₂ 3-I 2-Me-4-CF₂CF₃ 118-120 1-302 OMe₂CH₂SO₂NEt₂ 3-I 2-Me-4-CF₂CF₃ Amorphous 1-303 OMe₂CH₂SO₂NHCH₂Ph 3-I 2-Me-4-CF₂CF₃ 153-154 1-304 OMe₂CH₂SO₂NHCH₂CH₂SMe 3-I 2-Me-4-CF₂CF₃ 164-166 1-305 OMe₂CH₂SO₂NHCH₂CH₂SOMe 3-I 2-Me-4-CF₂CF₃ 150-152 1-306 OMe₂CH₂SO₂NHCH₂CH₂SO₂Me 3-I 2-Me-4-CF₂CF₃ 139-142 1-307 OMe₂CH₂SO₂NHCH₂CH₂SEt 3-I 2-Me-4-CF₂CF₃ 159-160 1-308 OMe₂CH₂SO₂NHCH₂CH₂SOEt 3-I 2-Me-4-CF₂CF₃ 198-199 1-309 OMe₂CH₂SO₂NHCH₂CH₂SO₂Et 3-I 2-Me-4-CF₂CF₃ 133-134 1-310 OMe₂CH₂SO₂NHCH₂CH₂SPh 3-I 2-Me-4-CF₂CF₃ 144-145 1-311 CHMeCH₂SO₂NHEt 3-I 2-Me-4-CF₂CF₂CF₃ 1-312 CHMeCH₂SO₂NHEt 3-I 2-Cl-4-CF₃ 1-313 CHMeCH₂SO₂NHEt 3-I 2-F-4-CF₂CF₃ 1-314 CHMeCH₂SO₂NHEt 3-I 2-Cl-4-CF₂CF₃ 1-315 CHMeCH₂SO₂NHEt 3-I 2-Cl-4-CF₂CF₂CF₃ 1-316 CHMeCH₂SO₂NHEt 3-I 2-F-4-CF(CF₃)₂ 1-317 CHMeCH₂SO₂NHEt 3-I 2-Cl-4-CF(CF₃)₂ 1-318 CHMeCH₂SO₂NHEt 3-I 2-Br-4-CF(CF₃)₂ 1-319 CHMeCH₂SO₂NHEt 3-I 2-I-4-CF(CF₃)₂ 1-320 CHMeCH₂SO₂NHEt 3-I 2-Et-4-CF(CF₃)₂ 1-321 CHMeCH₂SO₂NHEt 3-I 2-n-Pr-4-CF(CF₃)₂ 1-322 CHMeCH₂SO₂NHEt 3-I 2-i-Pr-4-CF(CF₃)₂ 1-323 CHMeCH₂SO₂NHEt 3-I 2-t-Bu-4-CF(CF₃)₂ 1-324 CHMeCH₂SO₂NHEt 3-I 2-Ph-4-CF(CF₃)₂ 1-325 CHMeCH₂SO₂NHEt 3-I 2-CH₂OH-4-CF(CF₃)₂ 1-326 CHMeCH₂SO₂NHEt 3-I 2-CH₂OMe-4-CF(CF₃)₂ 1-327 CHMeCH₂SO₂NHEt 3-I 2-OMe-4-CF(CF₃)₂ 1-328 CHMeCH₂SO₂NHEt 3-I 2-SMe-4-CF(CF₃)₂ 1-329 CHMeCH₂SO₂NHEt 3-I 2-N(Me)₂-4-CF(CF₃)₂ 1-330 CHMeCH₂SO₂NHEt 3-I 2-NO₂-4-CF(CF₃)₂ 1-331 CHMeCH₂SO₂NHEt 3-I 2-CF₃-4-CF(CF₃)₂ 1-332 CHMeCH₂SO₂NHEt 3-I 2-CHO-4-CF(CF₃)₂ 1-333 CHMeCH₂SO₂NHEt 3-I 2-CN-4-CF(CF₃)₂ 1-334 CHMeCH₂SO₂NHEt 3-I 2-COMe-4-CF(CF₃)₂ 1-335 CHMeCH₂SO₂NHEt 3-I 2,3-(Me)₂-4-CF(CF₃)₂ 1-336 CHMeCH₂SO₂NHEt 3-I 2-Me-3-F-4-CF(CF₃)₂ 1-337 CHMeCH₂SO₂NHEt 3-I 2-Me-3-Cl-4-CF(CF₃)₂ 1-338 CHMeCH₂SO₂NHEt 3-I 2-Me-3-OH-4-CF(CF₃)₂ 1-339 CHMeCH₂SO₂NHEt 3-I 2-Me-3-OMe-4-CF(CF₃)₂ 1-340 CHMeCH₂SO₂NHEt 3-I 2-Me-5-F-4-CF(CF₃)₂ 1-341 CHMeCH₂SO₂NHEt 3-I 2-Me-5-Cl-4-CF(CF₃)₂ 1-342 CHMeCH₂SO₂NH₂ 3-I 2-Me-4-CH(CF₃)₂ 214-216 1-343 CHMeCH₂SO₂NHEt 3-I 2-Me-4-CH(CF₃)₂ 232-234 1-344 OMe₂CH₂SO₂NEt₂ 3-I 2-Me-4-CH(CF₃)₂ Amorphous 1-345 OMe₂CH₂SO₂N(CH₂)₄ 3-I 2-Me-4-CH(CF₃)₂ Amorphous 1-346 CHMeCH₂SO₂NHEt 3-I 2-Me-4-C(OH)(CF₃)₂ 1-347 CHMeCH₂SO₂NHEt 3-I 2-Me-4-C(OMe)(CF₃)₂ 1-343 CHMeCH₂SO₂NHEt 3-I 2-Me-4-C(OEt)(CF₃)₂ 1-349 CHMeCH₂SO₂NHEt 3-I 2-OCF₂O-3-4-CF(CF₃)₂ 1-350 CHMeCH₂SO₂NHEt 3-I 2-OCH₂O-3-4-CF(CF₃)₂ 1-351 CHMeCH₂SO₂NHEt 3-I 2-(CH₂)₃-3-4-CF(CF₃)₂ 1-352 CHMeCH₂SO₂NHEt 3-I 2-(CH₂)₄-3-4-CF(CF₃)₂ 1-353 CHMeCH₂SO₂NHEt 3-I 2-Me-4-CF(CF₃)CF₂CF₃

TABLE 2 General formula (I-2) (I-2)

Physical property: Melting No. —A—SO₂NR¹R² Xm Yn point ° C. 2-1 CHMeCH₂SO₂NHEt 3-I 4-CF(CF₃)₂ 2-2 CHMeCH₂SO₂NH₂ 3-I 2-Me-4-CF(CF₃)₂ 2-3 CHMeCH₂SO₂NHMe 3-I 2-Me-4-CF(CF₃)₂ 2-4 CHMeCH₂SO₂NMe₂ 3-I 2-Me-4-CF(CF₃)₂ 2-5 CHMeCH₂SO₂NHEt 3-I 2-Me-4-CF(CF₃)₂ Amor- phous 2-6 CHMeCH₂SO₂NEt₂ 3-I 2-Me-4-CF(CF₃)₂ 2-7 CMe₂CH₂SO₂NEt₂ 3-I 2-Me-4-CF(CF₃)₂ Amor- phous 2-8 CHMeCH₂SO₂NHEt 3-I 2-Cl-4-CF(CF₃)₂ 2-9 CHMeCH₂SO₂NHEt 3-I 2-OMe-4-CF(CF₃)₂ 2-10 CHMeCH₂SO₂NHEt 3-I 2-SMe-4-CF(CF₃)₂ 2-11 CHMeCH₂SO₂NHEt 3-I 2-SOMe-4-CF(CF₃)₂ 2-12 CHMeCH₂SO₂NHEt 3-I 2-SO₂Me-4-CF(CF₃)₂ 2-13 CHMeCH₂SO₂NHEt 3-I 2-Et-4-CF(CF₃)₂ 2-14 CHMeCH₂SO₂NHEt 3-I 2-n-Pr-4-CF(CF₃)₂ 2-15 CHMeCH₂SO₂NHEt 3-I 4-CH(CF₃)₂ 2-16 CHMeCH₂SO₂NHEt 3-I 2-Me-4-CH(CF₃)₂ Amor- phous 2-17 CHMeCH₂SO₂NHEt 3-I 2-Cl-4-CH(CF₃)₂ 2-18 CHMeCH₂SO₂NHEt 3-I 2-OMe-4-CH(CF₃)₂ 2-19 CHMeCH₂SO₂NHEt 3-I 2-SMe-4-CH(CF₃)₂ 2-20 CHMeCH₂SO₂NHEt 3-I 2-SOMe-4-CH(CF₃)₂ 2-21 CHMeCH₂SO₂NHEt 3-I 2-SO₂Me-4-CH(CF₃)₂ 2-22 CHMeCH₂SO₂NHEt 3-I 2-Et-4-CH(CF₃)₂ 2-23 CHMeCH₂SO₂NHEt 3-I 2-n-Pr-4-CH(CF₃)₂

Table 3 shows ¹H-NMR data of compounds having a physical property expressed by the word “amorphous” in Table 1 and Table 2. TABLE 3 NMR data No. ¹H-NMR[CDCl₃ (or DMSO-d₆)/TMS, δvalues (ppm)] 1-62 1.30(d, 3H), 1.60(s, 6H), 2.38(s, 3H), 2.80(m, 2H), 3.30(m, (CDCl₃) 3H), 3.43(s, 2H), 4.00(m, 1H), 4.50(m, 1H), 6.45(br, 1H), 7.25(m, 1H), 7.48(m, 2H), 7.76(d, 1H), 7.98(d, 1H), 8.29(d, 1H), 8.40(br, 1H) 1-147 1.09(d, 3H), 1.44(d, 3H), 2.05(s, 3H), 2.37(s, 3H), 2.43(m, (CDCl₃) 2H), 3.32(m, 2H), 3.63(m, 1H), 4.63(m, 1H), 5.46(br, 1H), 6.70(br, 1H), 7.21(t, 1H), 7.36(d, 1H), 7.44(s, 1H), 7.70(d, 1H), 7.90(m, 2H), 8.64(br, 1H) 1-149 1.19(d, 3H), 1.37(d, 3H), 2.33(s, 3H), 2.83(s, 3H), 3.52(m, (CDCl₃) 2H), 3.27(d, 2H), 3.98(m, 1H), 4.55(m, 1H), 5.98(br, 1H), 6.88(br, 1H), 7.11(t, 1H), 7.33(d, 1H), 7.42(s, 1H), 7.60(m, 1H), 7.83(m, 2H), 8.89(br, 1H) 1-175 1.49(s, 6H), 2.35(s, 3H), 3.65(s, 2H), 6.91(br, 2H), 7.25(m, (DMSO-d₆) 1H), 7.51(d, 1H), 7.52(s, 1H), 7.70(d, 1H), 7.78(d, 1H), 7.99(d, 1H), 8.29(s, 1H), 9.87(br, 1H) 1-176 1.63(s, 6H), 2.39(s, 3H), 2.56(d, 3H), 3.41(s, 2H), 4.21(br, (CDCl₃) 1H), 6.48(br, 1H), 7.20(m, 1H), 7.47(m, 2H), 7.74(d, 1H), 7.99(d, 1H), 8.30(br, 1H), 8.32(d, 1H) 1-178 1.01(t, 3H), 1.61(s, 6H), 2.38(s, 3H), 2.98(q, 2H), 3.40(s, (CDCl₃) 2H), 4.52(br, 1H), 6.63(br, 1H), 7.19(m, 1H), 7.43(m, 2H), 7.71(d, 1H), 7.95(d, 1H), 8.21(d, 1H), 8.46(br, 1H) 1-179 1.08(t, 6H), 1.61(s, 6H), 2.34(s, 3H), 3.12(q, 4H), 3.21(s, (CDCl₃) 2H), 6.75(br, 1H), 7.20(m, 1H), 7.43(m, 2H), 7.75(d, 1H), 7.96(d, 1H), 8.37(d, 1H), 8.50(br, 1H) 1-266 1.00(t, 3H), 1.28(d, 3H), 2.84(m, 4H), 4.27(m, 1H), (DMSO-d₆) 7.14(br, 1H), 7.28(m, 1H), 7.67(m, 3H), 8.03(d, 1H), 8.52(d, 1H), 10.14(br, 1H) 1-276 1.10(t, 6H), 1.46(d, 3H), 2.31(s, 3H), 3.15(m, 5H), 3.67(m, (CDCl₃) 1H), 4.60(m, 1H), 6.80(br, 1H), 7.04(s, 1H), 7.21(t, 1H), 7.25(d, 1H), 7.74(d, 1H), 7.95(d, 1H), 8.01(d, 1H), 8.26(br, 1H) 1-277 1.11(t, 6H), 1.63(s, 6H), 2.33(s, 3H), 3.14(q, 4H), 3.20(s, (CDCl₃) 2H), 6.67(br, 1H), 7.12(d, 1H), 7.21(m, 2H), 7.77(d, 1H), 7.97(d, 1H), 8.18(d, 1H), 8.30(br, 1H) 1-302 1.10(t, 6H), 1.62(s, 6H), 2.38(s, 3H), 3.12(q, 4H), 3.16(s, (CDCl₃) 2H), 6.68(br, 1H), 7.22(m, 1H), 7.43(m, 2H), 7.79(d, 1H), 7.99(d, 1H), 8.43(br, 1H), 8.45(d, 1H) 1-344 1.09(t, 6H), 1.62(s, 6H), 2.35(s, 3H), 3.13(q, 4H), 3.20(s, (CDCl₃) 2H), 3.99(m, 1H), 6.63(br, 1H), 7.26(m, 3H), 7.78(d, 1H), 7.98(d, 1H), 8.33(d, 1H), 8.35(br, 1H) 1-345 1.63(s, 6H), 1.78(m, 4H), 2.35(s, 3H), 3.19(m, 4H), 3.26(s, (CDCl₃) 2H), 3.99(m, 1H), 6.68(br, 1H), 7.23(m, 3H), 7.77(d, 1H), 7.98(d, 1H), 8.31(d, 1H), 8.33(br, 1H) 2-5 1.05(t, 3H), 1.47(d, 3H), 2.59(s, 3H), 3.05(m, 2H), 3.25(d, (CDCl₃) 2H), 4.50(m, 1H), 5.05(br, 1H), 6.65(br, 1H), 7.25(m, 1H), 7.45(d, 1H), 7.73(d, 1H), 7.97(d, 1H), 8.33(d, 1H), 8.63(br, 1H) 2-7 1.08(t, 6H), 1.63(s, 6H), 2.62(s, 38), 3.12(q, 4H), 3.18(s, (CDCl₃) 2H), 6.79(br, 1H), 7.22(m, 1H), 7.53(d, 1H), 7.77(d, 1H), 7.98(d, 1H), 8.73(d, 1H), 8.78(br, 1H) 2-16 1.01(t, 3H), 1.46(d, 3H), 2.55(s, 3H), 3.03(m, 2H), 3.24(d, (CDCl₃) 2H), 4.40(m, 2H), 5.10(br, 1H), 6.65(br, 1H), 7.25(m, 2H), 7.71(d, 1H), 7.93(d, 1H), 8.14(d, 1H), 8.74(br, 1H)

EXAMPLES

Typical examples of the present invention are described below but they should not be construed as limiting the scope of the invention.

Example 1

Production of N²-(2-ethylsulfamoyl-1-methylethyl)-3-iodo-N′-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}phthalamide (compound No. 1-4)

(1-1) In tetrahydrofuran (500 ml) was dissolved 22.53 g (300 mmol) of 2-aminopropanol, and then 155.1 g (300 mmol) of a 30% solution of carbobenzoxy chloride in toluene and a solution of 36.43 g (360 mmol) of triethylamine in tetrahydrofuran were slowly dropped thereinto under ice-cooling. After the resulting mixture was stirred at room temperature for 3 hours, the triethylamine hydrochloride precipitated was filtered under reduced pressure and washed with ethyl acetate. The filtrate was concentrated under reduced pressure and diluted hydrochloric acid was added thereto, followed by three runs of extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and then saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then distilled to remove the solvent, whereby 49.8 g (yield 79%) of benzyl (2-hydroxy-1-methylethyl)carbamate was obtained.

(1-2) In tetrahydrofuran (400 ml) were dissolved 46.5 g (222 mmol) of benzyl (2-hydroxy-1-methylethyl)carbamate and 26.96 g (266 mmol) of triethylamine, and a solution of 27.96 g (244 mmol) of methanesulfonyl chloride in tetrahydrofuran was slowly dropped thereinto at 0° C. After the resulting mixture was stirred at room temperature for 5 hours, the triethylamine hydrochloride precipitated was filtered under reduced pressure and washed with ethyl acetate. The filtrate was concentrated under reduced pressure and water was added thereto, followed by three runs of extraction with ethyl acetate. The extract solution was washed with saturated aqueous sodium hydrogencarbonate solution and then saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was distilled off and the crude crystals thus obtained were washed twice with a solvent (hexane:ethyl acetate=4:1) to obtain 49.5 g (yield 78%) of 2-(benzyloxycarbonylamino)propyl methanesulfonate.

(1-3) In ethanol (120 ml) was dissolved 34.9 g (120 mmol) of 2-(benzyloxycarbonylamino)propyl methanesulfonate, followed by adding dropwise thereto a thiolate separately prepared from 14.42 g (120 mmol) of thioglycolic acid and a solution of sodium ethoxide (120 mmol) in ethanol. The reaction was carried out at room temperature for 30 minutes and then at 50° C. for 2 hours, after which the solvent was distilled off and water was added to the residue, followed by three runs of extraction with ethyl acetate. The extract solution was washed with saturated aqueous sodium hydrogencarbonate solution and then saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was distilled off and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to obtain 34.5 g (yield 92%) of 2-(benzyloxycarbonylamino)propylthioacetic acid.

(1-4) In ethyl acetate (150 ml) was dissolved 34.5 g (110 mmol) of 2-(benzyloxycarbonylamino)propylthioacetic acid, and a solution (50 ml) of 23.9 g (110 mmol) of m-chloroperbenzoic acid in ethyl acetate was slowly dropped thereinto at 0° C. After the reaction was carried out at room temperature for 3 hours, the reaction solution was poured into saturated aqueous sodium hydrogencarbonate solution, followed by extraction with ethyl acetate. The extract solution was washed three times with saturated aqueous sodium hydrogencarbonate solution and then once with saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was distilled off and the crude crystals thus obtained were washed twice with a solvent (hexane:ethyl acetate=2:1) to obtain 30.38 g (yield 84%) of 2-(benzyloxycarbonylamino)propylsulfinylacetic acid.

(1-5) In methanol (300 ml) was suspended 30.38 g (93 mmol) of 2-(benzyloxycarbonylamino)propylsulfinylacetic acid, followed by adding thereto 19.04 g (75 mmol) of iodine, and the reaction was carried out with refluxing for 5 hours. An aqueous sodium hydrogensulfite solution was added to the reaction mixture to reduce the excess iodine, after which the solution thus obtained was made weakly basic with saturated aqueous sodium hydrogencarbonate solution and sodium hydrogencarbonate and the methanol was distilled off. Water was added to the residue, followed by three runs of extraction with ethyl acetate. The extract solution was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate.

The solvent was distilled off and the thus obtained crude bis[2-(benzyloxycarbonylamino)propyl]-disulfide (29 mmol, estimated from ¹H-NMR integral ratio) was suspended in ethanol (150 ml), followed by adding thereto 15.66 g (88 mmol) of N-bromosuccinimide in small portions. The reaction was carried out at room temperature for 3 hours, after which the reaction solution was made weakly basic with saturated aqueous sodium hydrogencarbonate solution and sodium hydrogencarbonate and the ethanol was distilled off. Water was added to the residue, followed by three runs of extraction with ethyl acetate. The extract solution was washed three times with water and then once with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain 16.0 g (yield 60%) of ethyl 2-(benzyloxycarbonylamino)propane-1-sulfinate.

(1-6) In ethanol (7 ml) was dissolved 2.2 g (7.4 mmol) of ethyl 2-(benzyloxycarbonylamino)propane-1-sulfinate, and 3.2 g (8 mmol) of 10% aqueous sodium hydroxide solution was slowly dropped thereinto under ice-cooling. The reaction was carried out at room temperature for 1 hour, after which the ethanol was distilled off and water was added to the residue, followed by two runs of extraction with methyl t-butyl ether. The aqueous layer was acidified with concentrated hydrochloric acid, followed by three runs of extraction with ethyl acetate. The extract solution was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off and the crude crystals thus obtained were washed twice with a solvent (hexane:ethyl acetate=4:1) to obtain 1.73 g (yield 91%) of 2-(benzyloxycarbonylamino)propane-1-sulfinic acid.

(1-7) In water (10 ml) was dissolved 0.52 g (3.8 mmol) of potassium carbonate and 1.73 g (6.7 mmol) of 2-(benzyloxycarbonylamino)propane-1-sulfinic acid was added thereto, after which 1.07 g (6.7 mmol) of bromine was added dropwise thereto (water was properly added because crystals were precipitated during the dropwise addition to make stirring difficult). After stirring at room temperature for 30 minutes, the crystals were filtered and then washed with water to obtain 2.30 g (quantitative) of 2-(benzyloxycarbonylamino)propane-1-sulfonyl bromide.

(1-8) A solution (5 ml) of 1.44 g (3.3 mmol) of 2-(benzyloxycarbonylamino)propane-1-sulfonyl bromide in tetrahydrofuran was added dropwise to 70% aqueous ethylamine solution (10 ml) under ice-cooling. The reaction was carried out at room temperature for 1 hour, after which the reaction mixture was poured into diluted hydrochloric acid, followed by three runs of extraction with ethyl acetate. The extract solution was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain crude N-ethyl-2-(benzyloxycarbonylamino)propane-1-sulfonamide, and this crude product was used without further purification in the subsequent reaction.

(1-9) In a bottle for pressure hydrogenation, the inner atmosphere of which had been replaced with argon, was placed 0.07 g of 10% Pd—C, and suspended by adding ethanol (10 ml) thereto all at once. Then, a solution (20 ml) of the crude N-ethyl-2-(benzyloxycarbonylamino)propane-1-sulfonamide obtained in (1-8) in ethanol was added thereto and the reaction was carried out for 10 hours under pressure (hydrogen pressure: 4 kg/cm²) (during the reaction, the pressure was reduced for reducing the partial pressure of carbon monoxide produced, and then was re-increased). The reaction solution was filtered with Celite and washed with ethanol, and the filtrate was concentrated under reduced pressure. The crystals thus obtained were washed twice with a solvent (hexane:ethyl acetate=2:1) to obtain 0.27 g {yield from 2-(benzyloxycarbonylamino)propane-1-sulfonyl bromide: 50%} of N-ethyl-2-aminopropane-1-sulfonamide.

(1-10) In acetonitrile (100 ml) was dissolved 5.5 g (20 mmol) of 3-iodophthalic anhydride, and a solution (20 ml) of 5.5 g (20 mmol) of 2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]aniline in acetonitrile was slowly dropped thereinto. After the resulting mixture was stirred at room temperature for 3 hours, two-thirds of the acetonitrile was distilled off under reduced pressure and the crystals precipitated were filtered and then washed with acetonitrile to obtain 5.6 g (yield 51%) of 6-iodo-N-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}phthalamic acid.

(1-11) In methyl t-butyl ether (60 ml) was suspended 5.47 g (10 mmol) of 6-iodo-N-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}phthalamic acid, and a solution of 3.15 g (15 mmol) of trifluoroacetic anhydride in methyl t-butyl ether was slowly dropped thereinto. The resulting mixture was stirred at room temperature for 3 hours and then poured into ice water, followed by three runs of extraction with ethyl acetate. The extract solution was washed twice with saturated aqueous sodium hydrogencarbonate solution and then once with saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was distilled off and the crude crystals thus obtained were washed twice with a solvent (hexane:ethyl acetate=4:1) to obtain 5.0 g (yield 94%) of 1,3-dihydro-7-iodo-3-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoro-methyl)ethyl]phenylimino}-2-benzofuran-1-one.

(1-12) In acetonitrile (10 ml) was dissolved 0.42 g (0.8 mmol) of 1,3-dihydro-7-iodo-3-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenylimino}-2-benzofuran-1-one, followed by adding thereto 0.13 g (0.8 mmol) of the N-ethyl-2-aminopropane-1-sulfonamide obtained in (1-9), and the reaction was carried out at room temperature for 10 hours. The solvent was distilled off and the crystals precipitated were filtered, and washed with acetonitrile and then with a mixed solvent (hexane:ethyl acetate=4:1) to obtain 0.45 g (yield 81%) of N²-(2-ethylsulfamoyl-1-methylethyl)-3-iodo-N′-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}phthalamide.

Melting point: 170-172° C.

Example 2

Production of 3-iodo-N¹-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N²-(2-sulfamoyl-1,1-dimethylethyl)phthalamide (compound No. 1-175)

(2-1) In tetrahydrofuran (300 ml) was dissolved 23.86 g (200 mmol) of 1,1-dimethyl-2-(methylthio)ethylamine, and 103.4 g (200 mmol) of a 30% solution of carbobenzoxy chloride in toluene and then a solution of 24.29 g (240 mmol) of triethylamine in tetrahydrofuran were slowly dropped thereinto under ice-cooling. After the resulting mixture was stirred at room temperature for 3 hours, the triethylamine hydrochloride precipitated was filtered under reduced pressure and washed with ethyl acetate. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to obtain 36.35 g (yield 72%) of benzyl 1,1-dimethyl-2-(methylthio)ethylcarbamate.

(2-2) To a solution of 45.4 g (179 mmol) of benzyl 1,1-dimethyl-2-(methylthio)ethylcarbamate in aqueous methanol (obtained by adding 5.22 g (290 mmol) of water to 150 ml of methanol) was added 33.46 g (188 mmol) of N-bromosuccinimide in small portions with stirring. The reaction was carried out at room temperature for 2 hours, after which the reaction solution was made weakly basic with saturated aqueous sodium hydrogencarbonate solution and then the methanol was distilled off. Water was added to the residue, followed by three runs of extraction with ethyl acetate. The extract solution was washed three times with water and then once with saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was distilled off and the thus obtained crude benzyl 1,1-dimethyl-2-(methylsulfinyl)ethylcarbamate was dissolved in acetic anhydride (150 ml), and the reaction was carried out with refluxing for 4 hours. The excess acetic anhydride and acetic acid were distilled off under reduced pressure to obtain a residue containing crude [2-(benzyloxycarbonylamino)-2-methylpropyl]thiomethyl acetate. This residue was dissolved in methanol (300 ml), followed by adding thereto 19.54 g (77 mmol) of iodine, and the reaction was carried out with refluxing for 5 hours. After the reaction mixture was cooled to room temperature, an aqueous sodium hydrogensulfite solution was added thereto to reduce the excess iodine. The reaction solution was made weakly basic with saturated aqueous sodium hydrogencarbonate solution, after which the methanol was distilled off. Water was added to the residue, followed by three runs of extraction with ethyl acetate. The extract solution was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to obtain 10.0 g (yield 23%) of bis[2-(benzyloxycarbonylamino)-2-methylpropyl]-disulfide.

(2-3) In ethanol (150 ml) was dissolved 10.0 g (21 mmol) of bis[2-(benzyloxycarbonylamino)-2-methylpropyl]disulfide, and 11.21 g (63 mmol) of N-bromosuccinimide was added thereto in small portions with stirring. The reaction was carried out at room temperature for 2 hours, after which the reaction solution was made weakly basic with saturated aqueous sodium hydrogencarbonate solution and the ethanol was distilled off. Water was added to the residue, followed by three runs of extraction with ethyl acetate. The extract solution was washed three times with water and then once with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain 10.45 g (yield 83%) of ethyl 2-(benzyloxycarbonylamino)-2-methypropane-1-sulfinate.

(2-4) In ethanol (10 ml) was dissolved 0.60 g (2 mmol) of ethyl 2-(benzyloxycarbonylamino)-2-methylpropane-1-sulfinate, and 0.9 g (2.2 mmol) of 10% aqueous sodium hydroxide solution was slowly dropped thereinto under ice-cooling. The reaction was carried out at room temperature for 1 hour and then the ethanol was distilled off. Water (10 ml), 0.18 g (2.2 mmol) of sodium acetate and 0.25 g (2.2 mmol) of hydroxylamine-O-sulfonic acid were added to the residue, and the reaction was carried out at room temperature for 1 hour. The reaction mixture was poured into water, followed by three runs of extraction with ethyl acetate. The extract solution was washed with saturated aqueous sodium hydrogencarbonate solution and then saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was distilled off and 0.49 g (yield 86%) of the thus obtained crude 2-(benzyloxycarbonylamino)-2-methylpropane-1-sulfonamide was used without further purification in the subsequent reaction.

(2-5) In a bottle for pressure hydrogenation, the inner atmosphere of which had been replaced with argon, was placed 0.20 g of 10% Pd—C, and suspended by adding acetic acid (5 ml) thereto all at once. Then, a solution (10 ml) of the 2-(benzyloxycarbonylamino)-2-methylpropane-1-sulfonamide obtained in (2-4) in acetic acid was added thereto and the reaction was carried out for 10 hours under pressure (hydrogen pressure: 4 kg/cm²) (during the reaction, the pressure was reduced for reducing the partial pressure of carbon monoxide produced, and then was re-increased). The reaction solution was filtered with Celite and washed with ethanol, after which the filtrate was concentrated under reduced pressure and the residue (crude 2-amino-2-methylpropane-1-sulfonamide acetate) was used without further purification in the subsequent reaction.

(2-6) In acetonitrile (10 ml) was dissolved 0.8 g (1.5 mmol) of 1,3-dihydro-7-iodo-3-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenylimino}-2-benzofuran-1-one, followed by adding thereto the crude 2-amino-2-methylpropane-1-sulfonamide acetate obtained in (2-5) and 0.17 g (1.7 mmol) of triethylamine, and the reaction was carried out at room temperature for 30 hours. The solvent was distilled off and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain 0.05 g (yield 9%) of 3-iodo-N¹-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N²-(2-sulfamoyl-1,1-dimethylethyl)phthalamide as an amorphous substance.

¹H-NMR [DMSO-d₆/TMS, 5 values (ppm)] 1.49(s, 6H), 2.35(s, 3H), 3.65(s, 2H), 6.91(br, 2H), 7.25(m, 1H), 7.51(d, 1H), 7.52(s, 1H), 7.70(d, 1H), 7.78(d, 1H), 7.99(d, 1H), 8.29(s, 1H), 9.87(br, 1H).

The agrohorticultural insecticides containing the sulfonamide derivative of general formula (I) or salt thereof of the present invention as an active ingredient are suitable for controlling various insect pests such as agrohorticultural insect pests, stored grain insect pests, sanitary insect pests, nematodes, etc., which are injurious to paddy rice, fruit trees, vegetables, other crops, flowers, ornamental plants, etc. They have a marked insecticidal effect, for example, on LEPIDOPTERA including summer fruit tortrix (Adoxophyes orana fasciata), smaller tea tortrix (Adoxophyes sp.), Manchurian fruit moth (Grapholita inopinata), oriental fruit moth (Grapholita molesta), soybean pod border (Leguminivora glycinivorella), mulberry leafroller (Olethreutes mori), tea leafroller (Caloptilia thevivora), Caloptilia sp. (Caloptilia zachrysa), apple leafminer (Phyllonorycter ringoniella), pear barkminer (Spulerrina astaurota), common white (Piers rapae crucivora), tobacco budworm (Heliothis sp.), codling moth (Laspey resia pomonella), diamondback moth (Plutella xylostella), apple fruit moth (Argyresthia conjugella), peach fruit moth (Carposina niponensis), rice stem borer (Chilo suppressalis), rice leafroller (Cnaphalocrocis medinalis), tobacco moth (Ephestia elutella), mulberry pyralid (Glyphodes pyloalis), yellow rice borer (Scirpophaga incertulas), rice skipper (Parnara guttata), rice armyworm (Pseudaletia separata), pink borer (Sesamia inferens), common cutworm (Spodoptera litura), beet armyworm (Spodoptera exigua), etc.; HEMIPTERA including aster leafhopper (Macrosteles fascifrons), green rice leafhopper (Nephotettix cincticeps), brown rice planthopper (Nilaparvata lugens), whitebacked rice planthopper (Sogatella furcifera), citrus psylla (Diaphorina citri), grape whitefly (Aleurolobus taonabae), sweetpotato whitefly (Bemisia tabaci), greenhouse whitefly (Trialeurodes vaporariorum), turnup aphid (Lipaphis erysimi), green peach aphid (Myzus persicae), Indian wax scale (Ceroplastes ceriferus), cottony citrus scale (Pulvinaria aurantii), camphor scale (Pseudaonidia duplex), san Jose scale (Comstockaspis perniciosa), arrowhead scale (Unaspis yanonensis), etc.; TYLENCHIDA including soybean beetle (Anomala rufocuprea), Japanese beetle (Popillia japonica), tobacco beetle (Lasioderma serricorne), powderpost beetle (Lyctus brunneus), twenty-eight-spotted ladybird (Epilachna vigintiotopunctata), azuki bean weevil (Callosobruchus chinensis), vegetable weevil (Listroderes costirostris), maize weevil (Sitophilus zeamais), boll weevil (Anthonomus grandis grandis), rice water weevil (Lissorhoptrus oryzophilus), cucurbit leaf beetle (Aulacophora femoralis), rice leaf beetle (Oulema oryzae), striped flea beetle (Phyllotreta striolata), pine shoot beetle (Tomicus piniperda), Colorado potato beetle (Leptinotarsa decemlineata), Mexican bean beetle (Epilachna varivestis), corn rootworm (Diabrotica sp.), etc.; DIPTERA including melon fly (Dacus(Zeugodacus) cucurbitae), oriental fruit fly (Dacus(Bactrocera) dorsalis), rice leafminer (Agromyza oryzae), onion maggot (Delia antiqua), seedcorn maggot (Delia platura), soybean pod gall midge (Asphondylia sp.), muscid fly (Musca domestica), house mosquito (Culex pipiens pipiens), etc.; TYLENCHIDA including root-lesion nematode (Pratylenchus sp.), coffee root-lesion nematode (Pratylenchus coffeae), potato cyst nematode (Globodera rostochiensis), root-knot nematode (Meloidogyne sp.), citrus nematode (Tylenchulus semipenetrans), Aphelenchus sp. (Aphelenchus avenae), chrysanthemum foliar (Aphelenchoides ritzemabosi), etc.; and ACARINA including citrus red mite (Panonychus citri), European red mite (Panonychus ulmi), carmine spider mite (Tetranychus cinnabarinus), Kanzawa spider mite (Tetranychus kanzawai Kishida), two-spotted spider mite (Tetranychus urticae Koch), pink tea rust mite (Acaphylla theae), pink citrus rust mite (Aculops pelekassi), purple tea mite (Calacarus carinatus), pear rust mite (Epitrimerus pyri), etc.

The agrohorticultural insecticide containing the sulfonamide derivative of general formula (I) or salt thereof of the present invention as an active ingredient has a marked controlling effect on the above-exemplified insect pests injurious to paddy field crops, upland crops, fruit trees, vegetables, other crops, flowers and ornamental plants, and the like. Therefore, the desired effect of the agrohorti-cultural insecticide of the present invention can be obtained by applying the agrohorticultural insecticide to the seeds, paddy field water, stalks and leaves of fruit trees, vegetables, other crops, flowers and ornamental plants, soil, etc., at a season at which the insect pests are expected to appear, before their appearance or at the time when their appearance is confirmed.

The agrohorticultural insecticide of the present invention is generally prepared into conveniently usable forms according to an ordinary manner for preparation of agrochemicals.

That is, the sulfonamide derivative of general formula (I) or a salt thereof and, optionally, an adjuvant are blended with a suitable inert carrier in a proper proportion and prepared into a suitable preparation form such as a suspension, emulsifiable concentrate, soluble concentrate, wettable powder, granules, dust, tablets, pack or the like through dissolution, dispersion, suspension, mixing, impregnation, adsorption or sticking.

The inert carrier usable in the present invention may be either solid or liquid. As a material usable as the solid carrier, there can be exemplified soybean flour, cereal flour, wood flour, bark flour, saw dust, powdered tobacco stalks, powdered walnut shells, bran, powdered cellulose, extraction residues of vegetables, powdered synthetic polymers or resins, clay (e.g. kaolin, bentonite, and acid clay), talcs (e.g. talc and pyrophyllite), silica powders or flakes {e.g. diatomaceous earth, silica sand, mica and white carbon (synthetic, high-dispersion silicic acid, also called finely divided hydrated silica or hydrated silicic acid, some of commercially available products contain calcium silicate as the major component)}, activated carbon, powdered sulfur, pumice, calcined diatomaceous earth, ground brick, fly ash, sand, calcium carbonate, calcium phosphate and other inorganic or mineral powders, plastic carriers (e.g. polyethylenes, polypropylenes and poly(vinylidene chloride)s), chemical fertilizers (e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, urea and ammonium chloride), and compost. These materials may be used alone or as a mixture of two or more thereof.

A material usable as the liquid carrier is selected from materials that have solubility in themselves or which are without such solubility but are capable of dispersing a compound as active ingredient with the aid of an adjuvant. The following are typical examples of the liquid carrier and can be used alone or as a mixture of two or more thereof: water; alcohols (e.g. methanol, ethanol, isopropanol, butanol and ethylene glycol), ketones (e.g. acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone and cyclohexanone), ethers (e.g. ethyl ether, dioxane, Cellosolve, dipropyl ether and tetrahydrofuran), aliphatic hydrocarbons (e.g. kerosene and mineral oils), aromatic hydrocarbons (e.g. benzene, toluene, xylene, solvent naphtha and alkylnaphthalenes), halogenated hydrocarbons (e.g. dichloroethane, chloroform, carbon tetrachloride and chlorobenzene), esters (e.g. ethyl acetate, diisopropyl phthalate, dibutyl phthalate and dioctyl phthalate), amides (e.g. dimethylformamide, diethylformamide and dimethylacetamide), nitriles (e.g. acetonitrile), and dimethyl sulfoxide.

The following are typical examples of the adjuvant, which are used depending upon purposes and used alone or in combination in some cases, or need not be used at all.

To emulsify, disperse, dissolve and/or wet a compound as active ingredient, a surfactant is used. As the surfactant, there can be exemplified polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene higher fatty acid esters, polyoxyethylene resinates, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkylarylsulfonates, naphthalenesulfonic acid condensation products, ligninsulfonates and higher alcohol sulfate esters.

Further, to stabilize the dispersion of a compound as active ingredient, tackify it and/or bind it, the adjuvants exemplified below may also be used, namely, there may also be used adjuvants such as casein, gelatin, starch, methyl cellulose, carboxymethyl cellulose, gum arabic, poly(vinyl alcohol)s, turpentine, bran oil, bentonite and ligninsulfonates.

To improve the flowability of a solid product, the following adjuvants may also be used, namely, there may be used adjuvants such as waxes, stearates, alkyl phosphates, etc.

Adjuvants such as naphthalenesulfonic acid condensation products and polycondensates of phosphates may be used as a peptizer for dispersible products.

Adjuvants such as silicone oil may also be used as a defoaming agent.

Further, if necessary, functional spreading agents, active enhancers such as metabolic decomposition inhibitor like piperonyl butoxide, antifreezing agents such as propylene glycol, antioxidants such as BHT, ultraviolet absorbers, and the like may also be added.

The content of the compound as active ingredient may be varied as required, and may be properly chosen in the range of 0.01 to 90 parts by weight per 100 parts by weight of the agrohorticultural insecticide. For example, in dusts or granules, the suitable content of the compound as active ingredient is from 0.01 to 50 parts by weight. In emulsifiable concentrates or flowable wettable powders, it is also from 0.01 to 50 parts by weight.

The agrohorticultural insecticide of the present invention is used to control a variety of insect pests in the following manner: it is applied to a crop on which the insect pests are expected to appear, or a site where appearance or growth of the insect pests is undesirable, as it is or after being properly diluted with or suspended in water or the like, in an amount effective for control of the insect pests.

The applying dosage of the agrohorticultural insecticide of the present invention is varied depending upon various factors such as a purpose, insect pests to be controlled, a growth stage of a plant, tendency of insect pests appearance, weather, environmental conditions, a preparation form, an application method, an application site and application time. It may be properly chosen in the range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg, (in terms of the compound as active ingredient) per 10 areas depending upon purposes.

The agrohorticultural insecticide of the present invention may be used in admixture with other agrohorticultural insecticides, acaricides, nematocides, fungicides, biotic pesticides or the like in order to expand both spectrum of controllable insect pest species and the period of time when effective application is possible or to reduce the dosage. Furthermore, the agrohorticultural insecticide of the present invention may be used in admixture with herbicides, plant growth regulators, fertilizers or the like, depending upon application situations.

Typical formulation examples and test examples of the present invention are described below but they should not be construed as limiting the scope of the invention.

As used in the formulation examples, the terms “part” and “parts” are by weight.

Formulation Example 1

Each compound listed in Table 1 or 2 10 parts Xylene 70 parts N-methylpyrrolidone 10 parts Mixture of polyoxyethylene nonylphenyl 10 parts ether and calcium alkylbenzenesulfonate

An emulsifiable concentrate was prepared by mixing uniformly the above ingredients to effect dissolution.

Formulation Example 2

Each compound listed in Table 1 or 2  3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts

A dust was prepared by mixing uniformly and grinding the above ingredients.

Formulation Example 3

Each compound listed in Table 1 or 2 5 parts Mixed powder of bentonite and clay 90 parts  Calcium ligninsulfonate 5 parts

Granules were prepared by mixing the above ingredients uniformly, and kneading the resulting mixture together with a suitable amount of water, followed by granulation and drying.

Formulation Example 4

Each compound listed in Table 1 or 2 20 parts Mixture of kaolin and synthetic 75 parts high-dispersion silicic acid Mixture of polyoxyethylene nonylphenyl  5 parts ether and calcium alkylbenzenesulfonate

A wettable powder was prepared by mixing uniformly and grinding the above ingredients.

Test Example 1 Insecticidal Effect on Diamond Back Moth (Plutella xylostella)

Adult diamond back moths were released and allowed to oviposit on a Chinese cabbage seedling. Two days after the release, the seedling having the eggs deposited thereon was immersed for about 30 seconds in a liquid chemical prepared by diluting a preparation containing each compound listed in Table 1 or 2 as an active ingredient to adjust the concentration to 50 ppm. After air-dryness, it was allowed to stand in a room thermostated at 25° C.

Six days after the immersion, the hatched insects were counted. The mortality was calculated according to the following equation and the insecticidal effect was judged according to the criterion shown below. The test was carried out with triplicate groups of 10 insects. ${{Corrected}\quad{mortality}\quad(\%)} = {\frac{\begin{matrix} {{Number}\quad{of}} \\ {{hatched}\quad{insects}} \\ {{in}\quad{untreated}\quad{group}} \end{matrix} - \begin{matrix} {{Number}\quad{of}} \\ {{hatched}\quad{insects}} \\ {{in}\quad{treated}\quad{group}} \end{matrix}}{\begin{matrix} {{Number}\quad{of}\quad{hatched}\quad{insects}} \\ {{in}\quad{untreated}\quad{group}} \end{matrix}} \times 100}$ Criterion for Judgment:

A - - - Mortality 100%

B - - - Mortality 99-90%

C - - - Mortality 89-80%

D - - - Mortality 79-50%

E - - - Mortality less than 50%

The result of the above test is shown in Table 4 below.

Test Example 2 Insecticidal Effect on Common Cutworm (Spodoptera litura)

A piece of cabbage leaf (cultivar: Shikidori) was immersed for about 30 seconds in a liquid chemical prepared by diluting a preparation containing each compound listed in Table 1 or 2 as an active ingredient to adjust the concentration to 50 ppm. After air-dryness, it was placed in a plastic Petri dish with a diameter of 9 cm and inoculated with second-instar larvae of common cutworm, after which the dish was closed and then allowed to stand in a room thermostated at 25° C. Eight days after the inoculation, the dead and alive were counted. The mortality was calculated according to the following equation and the insecticidal effect was judged according to the criterion shown in Test Example 1. The test was carried out with triplicate groups of 10 insects. ${{Corrected}\quad{mortality}\quad(\%)} = {\frac{\begin{matrix} {{Number}\quad{of}} \\ {{alive}\quad{larvae}\quad{in}} \\ {{untreated}\quad{group}} \end{matrix} - \begin{matrix} {{Number}\quad{of}} \\ {{alive}\quad{larvae}\quad{in}} \\ {{treated}\quad{group}} \end{matrix}}{\begin{matrix} {{Number}\quad{of}\quad{alive}\quad{larvae}} \\ {{in}\quad{untreated}\quad{group}} \end{matrix}} \times 100}$

The result of the above test is shown in Table 4 below.

Test Example 3 Insecticidal Effect on Smaller Tea Tortrix (Adoxophyes sp.)

Tea leaves were immersed for about 30 seconds in a liquid chemical prepared by diluting a preparation containing each compound listed in Table 1 or 2 as an active ingredient to adjust the concentration to 50 ppm. After air-dryness, the tea leaves were placed in a plastic Petri dish with a diameter of 9 cm and inoculated with larvae of smaller tea tortrix, after which the dish was allowed to stand in a room thermostated at 25° C. and having a humidity of 70%. Eight days after the inoculation, the dead and alive were counted and the insecticidal effect was judged according to the criterion shown in Test Example 1. The test was carried out with triplicate groups of 10 insects.

The result of the above test is shown in Table 4 below. TABLE 4 No Test Example 1 Test Example 2 Test Example 3 1-1  A A A 1-2  A A A 1-3  A A A 1-4  A A A 1-6  A A A 1-7  A A A 1-8  A A A 1-12 A A A 1-14 A A A 1-20 A A A 1-21 A A A 1-22 A A A 1-23 A A A 1-24 A A A 1-25 A A A 1-27 A A A 1-28 A A A 1-29 A A A 1-30 A A A 1-31 A A A 1-32 A A A 1-35 A A A 1-36 A A A 1-37 A A A 1-38 A A A 1-39 A A A 1-40 A A A 1-41 A A A 1-42 A A A 1-43 A A A 1-44 A A A 1-45 A A A 1-46 A A A 1-47 A A A 1-48 A C A 1-54 A A A 1-55 A A A 1-56 A A A 1-57 A A A 1-58 A A E 1-59 A A E 1-60 A A E 1-61 A A A 1-62 A A A 1-63 A A A 1-66 A A A 1-67 A E E 1-71 A A A 1-72 A A A 1-73 A A A 1-75 A A A 1-76 A A A 1-77 A A A 1-78 A E A 1-79 A A A 1-80 A A A 1-81 A A A 1-82 A A A 1-83 A A A 1-84 A A A 1-85 A A A 1-86 A A A 1-87 A A A 1-88 A A A 1-89 A A A 1-91 A A A 1-92 A A A 1-93 A A A 1-94 A A A  1-103 A A A  1-104 A A A  1-105 A A E  1-106 A E E  1-107 A C A  1-108 A A A  1-109 A E A  1-110 A E E  1-111 A E E  1-112 A E E  1-116 A D A  1-121 A E E  1-142 A A A  1-144 A A A  1-146 A A A  1-147 A A A  1-148 A A A  1-149 A A A  1-175 A A A  1-176 A A A  1-177 A A A  1-178 A A A  1-179 A A A  1-180 A C A  1-181 A A A  1-184 A A A  1-200 A A A  1-201 A A A  1-207 A A E  1-208 A E A  1-211 A A A  1-212 A A A  1-213 A A A  1-214 A A A  1-215 A A A  1-216 A A A  1-217 A A A  1-218 A A A  1-219 A A A  1-266 A C E  1-267 A C E  1-268 A A A  1-275 A E E  1-276 A E E  1-277 A A A  1-285 A C E  1-286 A A E  1-301 A A A  1-302 A A A  1-303 A A A  1-304 A A A  1-305 A A A  1-306 A A A  1-307 A A A  1-308 A A A  1-309 A A A  1-310 A A A  1-342 A A A  1-343 A A A  1-344 A A A  1-345 A A A 2-5  A A A 2-7  A A A 2-16 A E A 

1. (canceled)
 2. (canceled)
 3. A sulfonamide derivative represented by general formula (1) or a salt thereof:

wherein A is a (C₁-C₆)alkylene group; R¹ is a hydrogen atom, a (C₁-C₆) alkyl group; a substituted (C₁-C₆)alkyl group having one or more substituents which may be the same or different and are selected from halogen atoms, hydroxyl group, (C₁-C₆) alkoxy groups, (C₁-C₆) alkylthio groups, (C₁-C₆) alkylsulfinyl groups, (C₁-C₆) alkylsulfonyl groups, (C₁-C₆) alkylaminocarbonyl groups, (C₁-C₆) alkylcarbonyloxy groups, phenylthio group, phenyl group, substituted phenyl groups having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, (C₁-C₆) alkoxy groups, halo (C₁-C₆) alkylthio groups, and pyridyl group; a (C₃-C₆) alkenyl group; a (C₃-C₆) alkynyl group; a (C₃-C₆)cycloalkyl group; a hydroxyl group; a (C₁-C₆)alkoxy group; an amino group, a phenylamino group, a substituted phenylamino group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, (C₁-C₆)alkoxy groups and (C₁-C₆)alkylthio groups; or a pyridyl group; each of R², R³ and R⁴, which may be the same or different, is a hydrogen atom, a (C₁-C₆)alkyl group, a (C₃-C₆) alkenyl group, a (C₃-C₆) alkynyl group, a (C₁-C₄) alkoxy(C₁-C₄)alkyl group or a (C₁-C₄) alkylthio(C₁-C₄ alkyl group, R² being able to bind to A or R¹ to form a 3- to 8-membered ring which may contain one to three atoms that may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, and which ring may have one or more substituents that may be the same or different and are selected from halogen atoms, (C₁-C₆) alkyl groups and (C₁-C₆) alkoxy groups; Q is a carbon atom or a nitrogen atom; each of Xs, which may be the same or different, is a halogen atom, a nitro group, a (C₁-C₆)alkyl group, a halo (C₁-C₆) alkyl group, a (C₂-C₆) alkenyl group, a halo (C₂-C₆) alkenyl group, a (C₂-C₆) alkynyl group halo (C₃-C₆) alkynyl group, a (C₁-C₆)alkoxy group, a halo (C₁-C₆) alkoxy group, a (C₁-C₆)alkylcarbonyloxy group, a halo(C₁-C₆)alkylcarbonyloxy group, a (C₁-C₆) alkylthio group, a halo (C₁-C₆) alkylthio group, a (C₁-C₆) aikylsulfinyl group, a halo (C₁-C₆) alkylsulfinyl group, a (C₁-C₆) alkylsulfonyl group, a halo(C₁-C₆)alkylsulfonyl group, a (C₁-C₆)alkylsulfonyloxy group or a haio(C₁-C₆)alkylsulfonyloxy group, two adjacent Xs on the aromatic ring being able to be taken together to represent a fused ring that may have one or more substituents which may be the same or different and are selected from halogen atoms, nitro group, cyano group, (C₁-C₆) alkyl groups, halo (C₁-C₆) alkyl groups, (C₁-C₆) alkoxy groups, halo (C₁-C₆) alkoxy groups, (C₁-C₆) alkylthio groups, halo (C₁-C₆) alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆) alkylsulfonyl groups and halo (C₁-C₆) alkylsulfonyi groups, m is an integer of 0 to 1: each of Ys, which may be the same or different, is a halogen atom; a (C₁-C₆)alkyl group; a halo (C₁-C₆) alkyl group; or a halo (C₁-C₆) alkoxy group; and n is an integer of 1 to
 3. 4. An agricultural and horticultural insecticide characterized by containing a sulfonamide derivative of general formula (I) or a salt thereof according to claim 3 as an active ingredient.
 5. A method for applying an agricultural and horticultural insecticide, characterized by treating a crop plant to be protected, soil or a paddy field with an effective amount of an agricultural and horticultural insecticide according to claim 4 in order to protect useful plants against insect pests. 